Sodium Carbonate → HCID 131732823, compound

Participants

Reaction Steps

To a solution of 4-Bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-isochromen-1-one (1.3 g, 3.53 mmol) in 15 ml of dioxane/H2O (5:1) was added 3,4-Difluorophenylboronic acid (0.83 g, 5.3 mmol) and Na2CO3(0.75 g, 7.06 mmol), then Pd(dppf)Cl2 (0.26 g, 0.35 mmol). Then the resultant mixture was stirred for 2 hours at 90° C. under N2. TLC showed SM was consumed, the reaction mixture was cooled to RT, removed the solvent, the residue was purified by column chromatography on silica gel eluted with (PE:EA=50:1) to afford title product. (m=1.3 g, yield=85%). 1HNMR: (400 MHz, CDCl3) δ 0.00 (s, 6 H), 0.83 (s, 9 H), 4.30 (tt, J=12 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 7.11 (t, J=6.0 Hz, 1H), 7.20 (m, 1H), 7.31 (tt, J=6.8 Hz, 1H), 7.54 (t, J=6.8 Hz, 1H), 7.64 (t, J=6.8 Hz, 1H), 8.36 (d, J=8.0 Hz, 1H).

Provenance & Evidence