Potassium Carbonate → HCID 11789046, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube containing methyl 2-bromo-4-methylbenzoate (650 mg, 2.84 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (781 mg, 3.55 mmol) and TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) (164 mg, 0.142 mmol) was evacuated and backfilled with nitrogen before Toluene (1.29E+04 μl) and Ethanol (1290 μl) were added, followed by K2CO3 (2838 μl, 5.68 mmol). The tube was heated in the microwave for 25 minutes at 130° C. The mixture was cooled, diluted with chloroform (15 mL), washed with aqueous ammonium chloride (saturated, 10 mL), dried (Na2 SO4), filtered and the solvent was evaporated under reduced pressure. The crude product was then purified by column chromatography on silica gel Isolute Flash Si; eluting with 5-10% EtOAc/isohexane to give 9-methyl-6H-benzo[c]chromen-6-one. 1H NMR (500 MHz; CDCl3): 8.32 (d, J=8.3 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.94 (s, 1H), 7.51 (m, 1H), 7.37 (m, 3H), 2.59 (s, 3H); LC-MS (IE, m/z): 211 [M+1]+.

Provenance & Evidence