Acetic Acid → (3-bromo-4-hydroxy-5-methoxy-phenyl)-acetic Acid Methyl Ester

HRID 547139Notes

Reaction equation

HRID 547139 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[C:13]([O:16][CH3:17])[C:14]=1[OH:15].[C:22](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:22][O:20][C:19](=[O:21])[CH2:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[C:14]([OH:15])=[C:9]([Br:8])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 5198053-Bromo-4-hydroxy-5-methoxyphenylacetic acid

Product 1

HCID 57443577(3-bromo-4-hydroxy-5-methoxy-phenyl)-acetic Acid Methyl EsterYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2 M solution in diethyl ether, 0.409 mL, 0.818 mmol) was added to a solution of (3-bromo-4-hydroxy-5-methoxy-phenyl)-acetic acid (150 mg, 0.575 mmol) in methanol (1 mL) and toluene (4 mL), and the mixture was stirred at room temperature for 30 minutes. Acetic acid was added to the reaction mixture to terminate the reaction, and then the mixture was concentrated under reduced pressure to give the target compound as a colorless oil (158 mg, 99%).

Workup

  1. customto terminate
  2. customthe reaction
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b9ba776c6794e07a24d95e6769726de
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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