Acetic Acid → Methyl 5-bromo-2-hydroxy-4-methoxybenzoate

HRID 629325Notes

Reaction equation

HRID 629325 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[N+](=[CH:16][Si](C)(C)C)=[N-].CCCCCC.C(O)(=O)C>CO>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 162174595-Bromo-2-hydroxy-4-methoxybenzoic acidHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 1051517Methyl 5-bromo-2-hydroxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-hydroxy-4-methoxybenzoic acid (2.00 g) in methanol (10.0 mL) was added 0.6M (diazomethyl)trimethylsilane/hexane solution (14.8 mL) under ice-cooling, and the mixture was stirred for 3 hr. To the reaction mixture was added acetic acid (0.12 mL), and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.08 g).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b00512c9328497187b53b1521c87cd5
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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