Acetic Acid → Methyl 2-(2-bromophenyl)acetate

HRID 547025Notes

Reaction equation

HRID 547025 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17].[C:19](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:19][O:17][C:16](=[O:18])[CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[Br:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 877542-Bromophenylacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2 M solution in diethyl ether, 0.349 mL, 0.698 mmol) was added to a solution of (2-bromo-phenyl)acetic acid (50 mg, 0.233 mmol) in methanol (0.4 mL) and toluene (2 mL), and the mixture was stirred at room temperature for five 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 (53 mg, 99%).

Workup

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

Sources & evidence

ORD record
ord-27021cadfb024c95b9475bd67aa9995b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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