Acetic Acid → Methyl 2-(3-bromo-4-methoxyphenyl)acetate

HRID 547128Notes

Reaction equation

HRID 547128 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[C:21](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:21][O:19][C:18](=[O:20])[CH2:17][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([Br:8])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1366153-Bromo-4-methoxyphenylacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 12717575Methyl 2-(3-bromo-4-methoxyphenyl)acetateYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2 M solution in diethyl ether, 0.306 mL, 0.612 mmol) was added to a solution of (3-bromo-4-methoxy-phenyl)-acetic acid (100 mg, 0.408 mmol) in methanol (1 mL) and toluene (4 mL), and the mixture was stirred at room temperature for 10 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 (100 mg, 95%).

Workup

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

Sources & evidence

ORD record
ord-7b984dce06474dbc82c70b7288e1c1aa
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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