Dichloromethane → Methyl 2-(3-bromophenyl)acetate

HRID 896654Notes

Reaction equation

HRID 896654 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.[CH2:12](Cl)Cl>>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetate

Procedure

To a solution of 3-bromophenylacetic acid (10 g, 46 mmol) in CH2Cl2 (20 mL) was added CH2N2 (Et2O) until yellow coloration persisted. The resulting reaction mixture was quenched with AcOH, and diluted with a NaHCO3 solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated to provided the (3-Bromo-phenyl)-acetic acid methyl ester compound.

Workup

  1. customThe resulting reaction mixture
  2. customwas quenched with AcOH
  3. additiondiluted with a NaHCO3 solution and ethyl acetate
  4. washThe organic extracts were washed (H2O, brine)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f48685f14164b6f93b21ceb71f185f4
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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