Methyl Salicylate → HCID 54767384, compound

Participants

Reaction Conditions

Reaction Steps

To 5 ml, of acetonitrile was added methyl 2-hydroxybenzoate (85 μL, 0.66 mmol), K2CO3 (273 mg, 2.0 mmol), and 4-bromomethylphenyl boronic acid pinacol ester (217 mg, 0.73 mmol). The reaction was heated to 70° C. under nitrogen overnight. After removal of the solvent via rotary evaporation, the resulting oil was brought up in EtOAc and washed with a saturated sodium bicarbonate solution to remove starting materials. The organic layer was dried over MgSO4, filtered and concentrated. The product was purified on a silica gel column eluting with 5% EtOAc in hexanes to yield B1 as a white solid in 77% yield (186 mg, 0.5 mmol). 1H NMR (400 MHz, CDCl3) δ=7.85-7.81 (m, 3H), 7.49 (d, J=7.6 Hz, 2H), 7.40 (dt, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.00-6.96 (m, 2H), 5.20 (s, 2H), 3.90 (s, 3H), 1.35 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=140.2, 135.2, 133.6, 132.0, 126.2, 121.0, 120.8, 114.0, 84.0, 70.7, 52.3, 25.1. ESI-MS(+): m/z 368.82 [M+H]+, 385.69 [M+NH4]+.

Provenance & Evidence