Boron tribromide → [4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Participants

Reaction Steps

To a stirred solution of (4-(2-chloroethoxy)phenyl)(4-methoxyphenyl)methanone (20 g, 1.0 eq) in 150 mL CH2Cl2 was added BBr3 (52 g, 3.0 eq) dropwise at 0° C. The reaction was stirred for 4 h at rt, then quenched with 500 mL ice water. The suspension was filtered and washed with water to give the product (16 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 10.36 (s, 1H), 7.69 (dd, J=6.8 Hz, 2.0 Hz, 2H), 7.64 (dd, J=6.8 Hz, 2.0 Hz, 2H), 7.11 (dd, J=7.2 Hz, 2.0 Hz, 2H), 6.90 (dd, J=6.8 Hz, 2.0 Hz, 2H), 4.38 (t, J=5.2 Hz, 2H), 4.01 (t, J=5.2 Hz, 2H).

Provenance & Evidence