Methanol → Methyl 2-(2-bromophenyl)acetate

HRID 1045783Notes

Reaction equation

HRID 1045783 reaction equation
CN(C)[CH:3]=[O:4].S(Cl)(Cl)=O.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18](O)=[O:19].CO>ClCCl>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]([O:4][CH3:3])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 877542-Bromophenylacetic acid

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add dimethylformamide (2.1 mL, 27.3 mmol) followed by thionyl chloride (52.3 mL, 717.8 mmol) over 7 minutes to a solution of 2-bromophenylacetic acid (150.0 g, 683.6 mmol) in dichloromethane (1.50 L) cooled with an ambient temperature water bath. Stir mixture for 5 hours, add methanol (41.5 mL, 1.0 mol) over 5 minutes. Bubble nitrogen through solution overnight. Concentrate to obtain the title compound as a colorless oil in quantitative yield (166.0 g, 724.7 mmol). 1H NMR (300 MHz, CDCl3): 7.57 (d, J=7.9 Hz, 1H), 7.30-7.26 (m, 2H), 7.19-7.12 (m, 1H), 3.80 (s, 2H), 3.72 (s, 3H).

Workup

  1. customthrough solution overnight
  2. concentrationConcentrate

Sources & evidence

ORD record
ord-e568c597f0be492fbe8d640baf9b3036
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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