Trimethylsilyldiazomethane → Methyl 4-bromo-3-fluorobenzoate

HRID 2085766Notes

Reaction equation

HRID 2085766 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-6725c954130f46858a5ac479252504be
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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