Dimethylformamide → 2-Amino-3-bromo-5-chlorobenzoic acid

HRID 251923Notes

Reaction equation

HRID 251923 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.[Br:17]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:10]([Br:17])=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 124762-Amino-5-chlorobenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 117799312-Amino-3-bromo-5-chlorobenzoic acidYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.7 g of 2-amino-5-chlorobenzoic acid and 100 ml of N,N-dimethylformamide was added 1.8 g of N-bromosuccinimide at room temperature, and the mixture was stirred at room temperature for 10 hours. Water was poured into the reaction mixture, and a deposited precipitate was collected by filtration to obtain 1.1 g of 2-amino-3-bromo-5-chlorobenzoic acid of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-5cce3e9f19aa4324b2fff2a463991124
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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