Hydrogen Bromide → 5-Acetyl-2-(4-bromo-2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 500567Notes

Reaction equation

HRID 500567 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([F:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].C1C(=O)N([Br:31])C(=O)C1.Br>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([F:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:31])=[CH:18][C:17]=1[Cl:22]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Product 1

HCID 865986395-Acetyl-2-(4-bromo-2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (251 mg, 0.739 mmol), NBS (139 mg, 0.781 mmol), and catalytic amount of HBr (48%) in DMF (3 mL) was stirred for 19 hours at room temperature. The reaction mixture was diluted with EtOAc, and washed with water (5×). The organic layer was dried over MgSO4, filtered, and concentrated to give the desired product (269 mg, 87%) that was used directly without further purification.

Workup

  1. washwashed with water (5×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-17e403e9239346ec82ea48a9b57a2657
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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