Bromine → 3-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acid

HRID 1982431Notes

Reaction equation

HRID 1982431 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:9])=[CH:6][CH:5]=1>C(OCC)C>[Br:1][CH:10]([C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:16][CH:15]=1)[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 1696663-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (2.6 ml) was added dropwise to a solution of 3-(4-chlorobenzoyl)propionic acid (10.6 g) in ethyl ether (200 ml) under stirring. The ethyl ether was distilled off to give 3-bromo-3-(4-chlorobenzoyl)propionic acid. Acetamide (30 g) was added thereto, and the mixture was heated with stirring on an oil bath at 140° C. for an hour. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the resulting crystalline precipitate was collected by filtration and washed with ethyl ether to give crystals of 4-(4-chlorophenyl)-2-methyloxazole-5-acetic acid, yield 3.9 g (31.1%). Recrystallization from ethanol gave needles, yield 3.5 g (27.9%), m.p. 215°-216° C.

Workup

  1. distillationThe ethyl ether was distilled off

Sources & evidence

ORD record
ord-0760399701034db49ce6f65b2019bd54
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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