(3-Bromophenyl)acetic acid → Methyl 2-(3-bromophenyl)acetate

HRID 1820255Notes

Reaction equation

HRID 1820255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:13]>C1C=CC=CC=1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74653(3-Bromophenyl)acetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 69.7%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A solution of 2-(3-bromophenyl)acetic acid (2.64 g, 12.28 mmol) in 8:2 benzene/methanol (50 mL) was cooled to 0° C., then treated with the dropwise addition of 2.0 M TMS-diazomethane in hexanes (6.14 mL, 12.28 mmol) over 10 minutes. The mixture was allowed to come to room temperature and stirred for 7 days. The mixture was concentrated in-vacuo, and the residue was purified over silica gel, eluting with 10% ethyl acetate/hexanes to yield the title compound (1.96 g, 8.56 mmol, 69.7% yield) as a colorless oil.

Workup

  1. customto come to room temperature
  2. concentrationThe mixture was concentrated in-vacuo
  3. customthe residue was purified over silica gel
  4. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ca438aade5b34f8780542f9c70d83891
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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