Trimethylsilyldiazomethane → 5-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 500557Notes

Reaction equation

HRID 500557 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[Si](C=[N+]=[N-])(C)(C)[CH3:22]>C1COCC1.CO>[CH3:22][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([F:20])=[C:4]([F:19])[C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 218669915-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

Product 1

HCID 865967715-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 99.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (17.4 g, 48.1 mmol) in THF-MeOH (100 mL-30 mL) was added TMSCHN2 (31.0 mL, 62.0 mmol, 2M solution in hexanes) at room temperature. The resulting mixture was stirred for 2 hours, quenched with AcOH, and diluted with EtOAc. The organic layer was washed with water, saturated NaHCO3 (2×), and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give the crude product (18.0 g, 99%) that was used directly without further purification.

Workup

  1. customquenched with AcOH
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water, saturated NaHCO3 (2×), and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce165ed14bd7422a92baacbf9abf18b7
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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