Water → (4-Bromo-3-methylphenyl)(4-hydroxyphenyl)methanone

Participants

Reaction Steps

A mixture of 65 (2.00 g, 6.55 mmol) and AlCl3 (3.50 g, 26.2 mmol) were refluxed in benzene (50 mL) for 3 h and then cooled to RT. Water (100 mL) was cautiously added dropwise, and the mixture was extracted with Et2O (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration afforded 1.78 g (93%) of 66 that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 2.45 (s, 3H), 5.68 (br s, 1H), 6.90 (d, J=8.6 Hz, 2H), 7.40 (dd, J=8.2 Hz, 1.8 Hz, 1H), 7.63 (m, 2H), 7.75 (d, J=8.6 Hz, 2H).

Provenance & Evidence