Acetic Acid → Methyl 2-(5-bromo-2-methoxyphenyl)acetate

HRID 547145

Reaction equation

HRID 547145 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH2:15][C:16]([OH:18])=[O:17])[CH:14]=1.[C:21](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:21][O:17][C:16](=[O:18])[CH2:15][C:13]1[CH:14]=[C:9]([Br:8])[CH:10]=[CH:11][C:12]=1[O:19][CH3:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 5553065-Bromo-2-methoxyphenylacetic acid

Product 1

HCID 21999895Methyl 2-(5-bromo-2-methoxyphenyl)acetateYield 98%

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 (5-bromo-2-methoxy-phenyl)-acetic acid (100 mg, 0408 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 (103.7 mg, 98%).

Workup

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

Sources & evidence

ORD record
ord-da01d3947f874f5b9db67375d3a68dac
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Linked notes

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