Dimethylformamide → 1,3,5-Trichloro-2-(chloromethyl)benzene

To a stirred solution of 2,4,6-trichlorobenzylalcohol (10.0 g; 47.3 mmoles) in chloroform (100 ml) kept under nitrogen atmosphere, thionyl chloride (6.07 mL, 85.1 mmole) was added slowly at 0° C. over a period of 15 minutes followed by catalytic amount of DMF. The reaction mix was allowed to stir at ambient temp for 3 hours. The reaction mixture was quenched with 50 mL of water; the aqueous layer was extracted with DCM (3×100 ml). The combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml) followed by brine (50 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. 10.9 g (100.0% of theory) of 1,3,5-trichloro-2-chloromethyl-benzene was obtained in form of a white solid.

1. additionThe reaction mix
2. customThe reaction mixture was quenched with 50 mL of water
3. extractionthe aqueous layer was extracted with DCM (3×100 ml)
4. washThe combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml)
5. dry with materialdried over anhydrous sodium sulphate
6. customThe solvent was evaporated under reduced pressure

ORD record

ord-92955a40f0944701a2c9764dbb71acf4

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258169B2