Dichloromethane → 2-[2-(Benzyloxy)-5-bromophenyl]acetic acid

HRID 1667635Notes

Reaction equation

HRID 1667635 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O.ClCCl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:19])=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 519916(2-Benzyloxyphenyl)acetic acid

Product 1

HCID 33070112-[2-(Benzyloxy)-5-bromophenyl]acetic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyloxyphenylacetic acid (242 mg, 11.0 mmol), N-bromosuccinimide (178 mg, 1.9 mmol) and dichloromethane (4 ml) was stirred overnight at room temperature under argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (280 mg, 87.2%) as a white solid.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-49aa1b2d6f084425be6a51c0c348cb6f
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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