Trimethylsilyldiazomethane → Methyl 4-bromo-3-fluorobenzoate

HRID 2356099Notes

Reaction equation

HRID 2356099 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-71cdb47433b74e97a0d5e2f3eedf3e78
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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