Hydrochloric Acid → 5-Bromo-2-(2,4-dichlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 500558Notes

Reaction equation

HRID 500558 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([F:11])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20].C1C(=O)N([Cl:29])C(=O)C1.Cl>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([F:11])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:29])=[CH:16][C:15]=1[Cl:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 865967715-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Product 1

HCID 865986345-Bromo-2-(2,4-dichlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.07 g, 5.50 mmol), NCS (789 mg, 5.91 mmol), and catalytic amount of conc. HCl in DMF (41 mL) was stirred for 1 hour 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 crude material which was purified by silica gel flash column chromatography (3 to 5% EtOAc in hexanes) to afford the desired product (2.02 g, 89%).

Workup

  1. washwashed with water (5×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude material which
  6. customwas purified by silica gel flash column chromatography (3 to 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ad98965cdfdb47918d349fa4da4c0ab2
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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