Bromochloromethane → 1-Chloromethanesulfonyl-4-fluoro-benzene

Temperature

100 °C

A stirred mixture of 4-fluoro-benzenesulfonyl chloride (10.16 g, 52.2 mmol), sodium sulfite (12.25 g, 97.1 mmol) and sodium bicarbonate (8.02 g, 95.5 mmol) in water (55 mL) is heated at 100° C. for 1 h. The crude sodium sulfinate solution is allowed to cool for 30 min and then treated with bromochloromethane (60 mL) and tetra-N-butyl ammonium bromide (1.68 g, 5.22 mmol). The resulting mixture is heated at 75° C. overnight. The organic layer was separated. The aqueous solution was extracted with CH2Cl2 (×2). The combined organics were washed with water and brine, and dried over anhydrous MgSO4. The filtration through Celite-silica gel pad and concentration in vacuo gave the desired product without further purification. 1H NMR (300 MHz, CDCl3) 8.00 (m, 2H), 7.30 (m, 2H), 4.53 (s, 2H).

1. temperatureto cool for 30 min
2. temperatureThe resulting mixture is heated at 75° C. overnight
3. customThe organic layer was separated
4. extractionThe aqueous solution was extracted with CH2Cl2 (×2)
5. washThe combined organics were washed with water and brine
6. dry with materialdried over anhydrous MgSO4
7. filtrationThe filtration
8. concentrationthrough Celite-silica gel pad and concentration in vacuo

ORD record

ord-4f0070da010e41599cb07fe778827ad4

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803793B2