Trimethylsilyldiazomethane → 6-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 1723680Notes

Reaction equation

HRID 1723680 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:5]([F:19])=[C:4]([F:20])[CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:22]>C1COCC1.CO>[CH3:22][O:9][C:8](=[O:10])[C:7]1[C:2]([Br:1])=[CH:3][C:4]([F:20])=[C:5]([F:19])[C:6]=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 860527636-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

Product 1

HCID 865985926-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (3.18 g, 8.77 mmol) in THF-MeOH (16 mL/5 mL) was added TMSCHN2 (5.30 mL, 10.6 mmol, 2 M solution in hexanes) at room temperature. The resulting mixture was stirred for 1 hour, 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 in vacuo to afford the desired product (3.31 g, 100%) 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 in vacuo

Sources & evidence

ORD record
ord-0600ea60d5944ac790e765603a38d910
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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