Water → HCID 86685517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-bromo-4-methylphenyl)propan-2-ol (19.2 g, 83.8 mmol) in DCM (100 mL) was added (chloromethoxy)ethane (15.85 g, 168 mmol) followed by addition of DIPEA (32.44 g, 251 mmol). The reaction mixture was stirred at 40° C. for 14 h. Water (200 mL) was added and the mixture was extracted three times with DCM. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give compound 2-bromo-2-(2-(ethoxymethoxy)propan-2-yl)-4-methylbenzene (21.8 g yield 91%) as yellow oil. 1H NMR (500 MHz, CDCl3): δ 7.38 (s, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.00 (d, J=8.0 Hz, 1H), 4.57 (s, 2 H), 3.58 (q, J=7.0 Hz, 2 H), 2.22 (s, 3H), 1.67 (s, 6H), 1.11 (t, J=7.0 Hz, 3 H) ppm.

Provenance & Evidence