Transition??Metal??Free Transformation of Aryl Bromides into Aromatic Esters and Amides via Aryl Trichloromethyl Ketones

S Dohi, K Moriyama, H Togo

Index: Dohi, Souya; Moriyama, Katsuhiko; Togo, Hideo European Journal of Organic Chemistry, 2013 , # 34 p. 7815 - 7822

Full Text: HTML

Citation Number: 3

Abstract

Abstract A variety of aryl bromides have been treated with Mg and then chloral, followed by tBuOCl and subsequently alcohols or amines to produce the corresponding aromatic esters or amides in good yields via the formation of aryl trichloromethyl ketones as intermediates. These reactions are examples of a transition-metal-free one-pot preparation of aromatic esters and amides from aryl bromides.

 Related Synthetic Route
4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

Benzamide,4-methyl-N-(phenylmethyl)- Structure

5436-83-9

Benzamide,4-met...

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

Benzylamine Structure

100-46-9

Benzylamine

~%

Benzamide,4-methyl-N-(phenylmethyl)- Structure

5436-83-9

Benzamide,4-met...

Tri-chloroacetylthiophene Structure

35320-25-3

Tri-chloroacety...

methylamine Structure

74-89-5

methylamine

~%

2-Thiophenecarboxamide,N-methyl-(6CI,7CI,9CI) Structure

39880-77-8

2-Thiophenecarb...

4-Bromobenzotrifluoride Structure

402-43-7

4-Bromobenzotri...

~%

N-methyl-4-(trifluoromethyl)benzamide Structure

65017-76-7

N-methyl-4-(tri...

2,2,2-trichloro-4'-(trifluoromethyl)acetophenone Structure

1370441-14-7

2,2,2-trichloro...

methylamine Structure

74-89-5

methylamine

~%

N-methyl-4-(trifluoromethyl)benzamide Structure

65017-76-7

N-methyl-4-(tri...

Bromobenzene Structure

108-86-1

Bromobenzene

~%

Benzenecarboximidic acid, N-methyl- (9CI) Structure

88070-48-8

Benzenecarboxim...

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

methylamine Structure

74-89-5

methylamine

~%

Benzenecarboximidic acid, N-methyl- (9CI) Structure

88070-48-8

Benzenecarboxim...

phenylmagnesium bromide Structure

100-58-3

phenylmagnesium...

~%

Benzenecarboximidic acid, N-methyl- (9CI) Structure

88070-48-8

Benzenecarboxim...

PHENYLMAGNESIUM CHLORIDE Structure

100-59-4

PHENYLMAGNESIUM...

~%

Benzenecarboximidic acid, N-methyl- (9CI) Structure

88070-48-8

Benzenecarboxim...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

N-METHYL-P-TOLUAMIDE Structure

18370-11-1

N-METHYL-P-TOLUAMIDE

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

methylamine Structure

74-89-5

methylamine

~%

N-METHYL-P-TOLUAMIDE Structure

18370-11-1

N-METHYL-P-TOLUAMIDE

Methanol Structure

67-56-1

Methanol

Tri-chloroacetylthiophene Structure

35320-25-3

Tri-chloroacety...

~%

2-(Carbomethoxy)thiophene Structure

5380-42-7

2-(Carbomethoxy...

Methanol Structure

67-56-1

Methanol

2,2,2-trichloro-1-(p-methoxyphenyl)ethanone Structure

36458-91-0

2,2,2-trichloro...

~%

Methyl anisate Structure

121-98-2

Methyl anisate

Bromobenzene Structure

108-86-1

Bromobenzene

Chloral Structure

75-87-6

Chloral

~82%

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

Chloral Structure

75-87-6

Chloral

phenylmagnesium bromide Structure

100-58-3

phenylmagnesium...

~91%

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

PHENYLMAGNESIUM CHLORIDE Structure

100-59-4

PHENYLMAGNESIUM...

Chloral Structure

75-87-6

Chloral

~90%

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

PHENYLMAGNESIUM CHLORIDE Structure

100-59-4

PHENYLMAGNESIUM...

Chloral Structure

75-87-6

Chloral

~84%

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

2,2,2-Trichloro-1-phenylethanol Structure

2000-43-3

2,2,2-Trichloro...

Chloral Structure

75-87-6

Chloral

phenylmagnesium bromide Structure

100-58-3

phenylmagnesium...

~65%

Ethanone,2,2,2-trichloro-1-phenyl- Structure

2902-69-4

Ethanone,2,2,2-...

2,2,2-Trichloro-1-phenylethanol Structure

2000-43-3

2,2,2-Trichloro...

Methanol Structure

67-56-1

Methanol

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

~%

methyl p-toluate Structure

99-75-2

methyl p-toluate

Chloral Structure

75-87-6

Chloral

phenylmagnesium bromide Structure

100-58-3

phenylmagnesium...

~94%

2,2,2-Trichloro-1-phenylethanol Structure

2000-43-3

2,2,2-Trichloro...

4-Bromoanisole Structure

104-92-7

4-Bromoanisole

~%

4-chloro-N-methyl-benzamide Structure

6873-44-5

4-chloro-N-meth...

2,2,2-trichloro-1-(p-methoxyphenyl)ethanone Structure

36458-91-0

2,2,2-trichloro...

methylamine Structure

74-89-5

methylamine

~%

4-chloro-N-methyl-benzamide Structure

6873-44-5

4-chloro-N-meth...

2,2,2-trichloro-1-(3-methylphenyl)ethanone Structure

124787-11-7

2,2,2-trichloro...

methylamine Structure

74-89-5

methylamine

~%

Benzamide, N,3-dimethyl- (9CI) Structure

74786-81-5

Benzamide, N,3-...

5-Bromo-1-benzothiophene Structure

7342-82-7

5-Bromo-1-benzo...

~%

Benzo[b]thiophene-3-carboxylic acid methyl ester Structure

22913-25-3

Benzo[b]thiophe...

1-Bromonaphthalene Structure

90-11-9

1-Bromonaphthalene

~%

N-methylnaphthalene-1-carboxamide Structure

3400-33-7

N-methylnaphtha...

4-Bromoanisole Structure

104-92-7

4-Bromoanisole

~%

Benzamide,4-methoxy-N-methyl- Structure

3400-22-4

Benzamide,4-met...

2,2,2-trichloro-1-(p-methoxyphenyl)ethanone Structure

36458-91-0

2,2,2-trichloro...

methylamine Structure

74-89-5

methylamine

~%

Benzamide,4-methoxy-N-methyl- Structure

3400-22-4

Benzamide,4-met...

2-Bromotoluene Structure

95-46-5

2-Bromotoluene

~%

Benzamide,N,2-dimethyl- Structure

2170-09-4

Benzamide,N,2-d...

N/A Structure

124787-10-6

N/A

methylamine Structure

74-89-5

methylamine

~%

Benzamide,N,2-dimethyl- Structure

2170-09-4

Benzamide,N,2-d...

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

Benzyl alcohol Structure

100-51-6

Benzyl alcohol

~%

benzyl 4-methylbenzoate Structure

5467-99-2

benzyl 4-methyl...

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

benzyl 4-methylbenzoate Structure

5467-99-2

benzyl 4-methyl...

Methanol Structure

67-56-1

Methanol

4-Bromochlorobenzene Structure

106-39-8

4-Bromochlorobenzene

t-Butyl hypochlorite Structure

507-40-4

t-Butyl hypochlorite

Chloral Structure

75-87-6

Chloral

~%

Detail
Methanol Structure

67-56-1

Methanol

N/A Structure

124787-10-6

N/A

~%

Methyl o-methylbenzoate Structure

89-71-4

Methyl o-methyl...

1-Bromonaphthalene Structure

90-11-9

1-Bromonaphthalene

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

2459-24-7

1-Naphthaleneca...

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

~%

4-Methylbenzamide Structure

619-55-6

4-Methylbenzamide

4-Bromotoluene Structure

106-38-7

4-Bromotoluene

~%

Methanone,(4-methylphenyl)-1-piperidinyl- Structure

13707-23-8

Methanone,(4-me...

Piperidine Structure

110-89-4

Piperidine

2,2,2-trichloro-1-(4-methylphenyl)ethanone Structure

36930-95-7

2,2,2-trichloro...

~%

Methanone,(4-methylphenyl)-1-piperidinyl- Structure

13707-23-8

Methanone,(4-me...


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved