Methyl iodide → Methyl 2-(4-bromophenyl)acetate

HRID 1264218Notes

Reaction equation

HRID 1264218 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOCC>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 99.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Bromo-phenyl-acetic acid (8.6 g, 40 mmol) in DMF (80 mL) is added K2CO3 (6.16 g, 44 mmol) followed by methyl iodide (2.8 mL, 45 mmol). The resulting mixture is stirred for 2.5 hours, then diluted with ether, washed with water and brine, dried over MgSO4 and concentrated to give 9.1 g of the title compound as an oil. This material is used without further purification. 1H NMR (CDCl3) d 3.58 (s, 2H), 3.69 (s, 3H), 7.13 (d, J=8 Hz, 2H), 7.43 (d, J=8 Hz, 2H). MS (EI) m/z 228/230 (M+) Br pattern.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-48c9cd91a70e44beb198aa37a87a8181
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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