Diazomethane → Methyl 2-bromo-4,5-difluorobenzoate

HRID 921248Notes

Reaction equation

HRID 921248 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:15])=[N-]>ClCCl.CO>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 27827892-Bromo-4,5-difluorobenzoic acid

Product 1

HCID 26985845Methyl 2-bromo-4,5-difluorobenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromo-4,5-difluorobenzoic acid (1 g, 4.22 mmol) in dichloromethane (10 mL) and MeOH (1 mL) was added trimethylsilyl)diazomethane (2.110 mL, 4.22 mmol) and the reaction was stirred at rt for 1 h. It was then concentrated to obtain methyl 2-bromo-4,5-difluorobenzoate (1 g, 3.98 mmol, 94% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.76 (dd, J=10.5, 8.3 Hz, 1H), 7.57-7.49 (m, 1H), 3.96 (s, 3H).

Workup

  1. concentrationIt was then concentrated

Sources & evidence

ORD record
ord-3a7832042e7c4f39a6729bffea61a210
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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