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

HRID 2427071Notes

Reaction equation

HRID 2427071 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F: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]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 27817032-Amino-3-bromo-5-fluorobenzoic acidYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.78 g of 2-amino-5-fluorobenzoic acid and 100 ml of N,N-dimethylformamide was added 1.1 g of N-bromosuccinimide at room temperature, and the mixture was stirred at room temperature for 5 hours. After water was added to the reaction mixture, a deposited precipitate was collected by filtration, and then washed with acetone to obtain 0.43 g of 2-amino-3-bromo-5-fluorobenzoic acid of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration
  2. washwashed with acetone

Sources & evidence

ORD record
ord-72520fe695d64cbcbcf3d7ed6d1d080a
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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