Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 896066Notes

Reaction equation

HRID 896066 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.[CH:12]1(N=C=NC2CCCCC2)CCCCC1.CO>ClCCl.CN(C)C1C=CN=CC=1>[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

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromophenylacetic acid (1.0 g, 4.65 mmol), 1,3-dicyclohexylcarbodiimide (1.44 g, 6.98 mmol) and MeOH (149 mg, 4.65 mmol) in dichloromethane (40 ml) was added 4-dimethylaminopyridine (57 mg, 0.465 mmol). The reaction mixture was stirred at RT for 1 hr. The white solid was precipitated out which was removed with filtration. The reaction solution was concentrated to give a crude product which was purified on silica gel column with dichloromethane. The product was collected which contain a little amount of DCU (1.36 g). NMR (CDCl3): □ 7.20-7.46 (4H, m), 3.72 (3H, s), 3.621(2H, s).

Workup

  1. customThe white solid was precipitated out which
  2. customwas removed with filtration
  3. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-817634e33cc7416ab9d7ed4d0adad243
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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