Water → 2-Bromo-1-methoxy-4-(methylsulfonyl)benzene

HRID 1420818Notes

Reaction equation

HRID 1420818 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1O.CI.O>CN(C)C=O>[Br:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:4][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 187826382-Bromo-4-(methylsulfonyl)phenol

Product 1

HCID 187826552-Bromo-1-methoxy-4-(methylsulfonyl)benzeneYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.31 g, 16.8 mmol) was added to a solution of 2-bromo-4-(methanesulfonyl)phenol (Description 27; 3.5 g, 14 mmol) in dimethylformamide (50 ml). The resulting solution was stirred for 30 min. and methyl iodide (1.04 ml, 16.8 mmol). After stirring for 1 h. the solution was poured into water (200 ml) and extracted with ethyl acetate (2×100 ml). The combined organics were washed with water and dried over sodium sulphate. Removal of the solvent in vacuo gave a white solid which was crystallised from diethyl ether to give the title compound (2.02 g). 1H NMR (250 MHz, CDCl3) δ8.12-8.11 (1H, d, J 2.2 Hz), 7.90-7.86 (1H, dd, J 8.7, 2.2 Hz), 7.04-7.00 (1H, d, J 8.7 Hz), and 3.99 (3H, s), and 3.05 (3H, s).

Workup

  1. stirringAfter stirring for 1 h. the solution
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organics were washed with water
  4. dry with materialdried over sodium sulphate
  5. customRemoval of the solvent in vacuo
  6. customgave a white solid which
  7. customwas crystallised from diethyl ether

Sources & evidence

ORD record
ord-1affdae42b834ab19f51bdc50aaea773
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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