5-bromo-3-methyl-3H-2-benzofuran-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-3-methyl-2-benzofuran-1(3H)-one (1.00 g, 4.40 mmol) was dissolved in toluene (30 mL) treated with lithium chloride (0.560 g, 13.2 mmol), Pd(Ph3P)4 (0.254 g, 0.220 mmol), and allyl tributylstannane (1.75 g, 5.29 mmol). The reaction mixture was degassed and stirred at reflux under N2 for 3 h. The reaction mixture was poured into water and extracted with ethyl acetate; the organic layer was washed wtih brine 1×, dried and purified by MPLC eluting with 0-10% ethyl acetate/hexanes. to afford the title compound. 1H NMR (500 MHz, D-DMSO, δ in ppm): 7.75 (d, J=8 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J=8 Hz, 1H), 6.00 (m, 1H), 5.66 (q, J=6.5 Hz, 1H), 5.13 (m, 2H), 3.53 (d, J=6.5 Hz, 2H), 1.54 (d, J=7 Hz, 3H). The reaction mixture was degassed at reflux under N2 for 3 h The reaction mixture was poured into water extracted with ethyl acetate the organic layer was washed wtih brine 1× dried purified by MPLC eluting with 0-10% ethyl acetate/hexanes