Water → 4-Bromo-1-(chloromethyl)-2-methylbenzene

Methanesulfonyl chloride (6.83 mL, 88.3 mmol) is added slowly to a solution of (4-bromo-2-methyl-phenyl)methanol (16.14 g, 80.27 mmol) and triethylamine (16.78 mL; 120.4 mmol) in dichloromethane (80.7 mL) cooled in ice/water. The mixture is allowed to slowly warm to ambient temperature and is stirred for 16 hours. Further methanesulfonyl chloride (1.24 mL; 16.1 mmol) is added and the mixture is stirred at ambient temperature for 2 hours. Water (80 mL) is added and the phases are separated. The organic layer is washed with hydrochloric acid (1N; 80 mL) then saturated aqueous sodium hydrogen carbonate solution (80 mL), then water (80 mL), and is dried over Na2SO4. Filtration and concentration under reduced pressure gives a residue which is purified by flash chromatography (eluting with hexane) to give the title compound (14.2 g; 80.5% yield). 1H NMR (300.11 MHz, CDCl3): δ 7.36-7.30 (m, 2H), 7.18 (d, J=8.1 Hz, 1H), 4.55 (s, 2H), 2.41 (s, 3H).

1. stirringthe mixture is stirred at ambient temperature for 2 hours
2. customthe phases are separated
3. washThe organic layer is washed with hydrochloric acid (1N; 80 mL)
4. dry with materialsaturated aqueous sodium hydrogen carbonate solution (80 mL), then water (80 mL), and is dried over Na2SO4
5. filtrationFiltration and concentration under reduced pressure
6. customgives a residue which
7. customis purified by flash chromatography (eluting with hexane)

ORD record

ord-5df139fa24f14e1891defe2ea0ebe2d5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697849B2