Water → HCID 86685505, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-bromo-5-chloro-4-methylphenyl)propan-2-ol (4.5 g 17.1 mmol), (chloromethoxy)ethane (3.2 g, 34.2 mmol) and DIPEA (6.6 g, 51.3 mmol) in DCM (50 mL) was stirred at 40° C. overnight under argon. Water (50 mL) was added and the mixture was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with PE-EA (10:1) to give 1-bromo-4-chloro-2-(2-(ethoxymethoxy)propan-2-yl)-5-methylbenzene (4.27 g, yield 77.5%). 1H NMR (400 MHz, DMSO-d6): δ 7.67 (s, 1H), 7.50 (s, 1H), 4.59 (s, 2H), 3.55 (q, 2H), 2.29 (s, 3H), 1.65 (s, 6H), 1.08 (t, 3H) ppm; MS: m/z=344.8 (M+Na+, ESI+).

Provenance & Evidence