Dimethyl Sulfate → 1-Chloro-2-(methoxymethyl)-4-(trifluoromethyl)benzene

A mixture of (2-chloro-5-(trifluoromethyl)phenyl)methanol (COK) (11.55 g, 55 mmol), NaOH (8.00 g, 200 mmol) and dimethyl sulfate (6.25 mL, 65 mmol) in THF (100 mL) was stired for 5 hours at room temperature. The reaction was quenched with water (20 mL) and 25% ammonia (5 mL) and the resulting mixture was stirred overnight at room temperature. The mixture was purred into water (100 mL) and extracted with petroleum ether (100 mL). The organic phase was washed with 1 M NaOH (aq) (100 mL), water (3×100 mL), brine (50 mL), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to yield 1-chloro-2-(methoxymethyl)-4-(trifluoromethyl)benzene (COMK) as a colorless oil (11.54 g, 94%): 1H NMR (CDCl3) 3.50 (s, 3H), 4.57 (s, 2H), 7.46 (m, 2H), 7.77 (s, 1H).

1. customThe reaction was quenched with water (20 mL) and 25% ammonia (5 mL)
2. extractionextracted with petroleum ether (100 mL)
3. washThe organic phase was washed with 1 M NaOH (aq) (100 mL), water (3×100 mL), brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customThe solvent was removed under reduced pressure

ORD record

ord-3f766ee56a0645d385e1e1099fed2676

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212118B2