Boron trifluoride etherate → 2-Bromo-4-(4-ethoxybenzyl)benzyl acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-4-(4-ethoxybenzoyl)benzyl acetate (0.41 g, 1.09 mmol) and Et3SiH (0.44 μL, 2.76 mmoL) in 1,2-dichloroethane/MeCN (2.5 mL, 1:2), was added dropwise BF3.Et2O (0.21 mL, 1.66 mmol). The reaction was complete after stirring for about 17 h at 25° C. Upon cooling, the reaction was quenched with 0.5 mL of 28.5% NaOH aqueous solution. The aqueous layer was extracted 2× with CH2Cl2, the combined organic layers were washed once with 2M KOH, 2× with H2O containing 10% brine and 2× with brine prior to drying over Na2SO4. After removal of the volatiles, the residue was purified by silica gel column (10:1 petroleum ether/ethyl acetate) to yield 0.24 g of title compound. 1H NMR (CDCl3, 300 MHz): δ 7.39 (s, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.07 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 5.15 (s, 2H), 4.01 (q, J=7.0 Hz, 2H), 3.88 (s, 2H), 2.12 (s, 3H), 1.40 (t, J=7.0 Hz, 3H); MS ESI (m/z) 380 (M+NH4)+, calc. 362.

Provenance & Evidence