Trimethylsilyldiazomethane → Methyl 4-bromo-3-fluorobenzoate

HRID 1785825Notes

Reaction equation

HRID 1785825 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].[CH3:12][Si](C=[N+]=[N-])(C)C>CO.ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 21951878Methyl 4-bromo-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-3-fluorobenzoic acid (117 mg, 0.50 mmol) in methanol (1 mL) and dichloromethane (2 mL) at room temperature was slowly treated with 2M trimethylsilyldiazomethane in hexanes until the solution became light yellow. The mixture was concentrated to provide the desired product.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-a7325f8acb1b42dbb1fbef3579193f1b
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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