3-Bromo-4-hydroxybenzoic acid → Methyl 3-bromo-4-hydroxybenzoate

HRID 1820957Notes

Reaction equation

HRID 1820957 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH3:12][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 843683-Bromo-4-hydroxybenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 3.9 g (18.0 mmol) of 3-bromo-4-hydroxybenzoic acid in 20 mL of 3:1 v/v CH2Cl2/CH3OH was treated with 10.8 mL of 2.0 M (trimethylsilyl)diazomethane solution in hexanes. The mixture was stirred at rt for 2 h, then concentrated to give 4.6 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 3.90 (s, 3H), 5.93 (bs, 1H), 7.05 (d, J=8.5, 1H), 7.92 (dd, J=2.1, 8.5, 1M), 8.19 (d, J=2.0, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-09f371757fd8402396466d2f4df78c2f
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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