Ethyl Acetate → HCID 13941270, compound

Participants

Reaction Steps

Methyl 3,5-dihydroxybenzoate (20 g., 0.12 mole, 1 eq), phenylboronic acid (30 g., 0.25 mole, 2.1 eq.), Copper II acetate (45 g., 0.25 mmole, 2.1 eq.), TEA (90 mL, 0.65 mmole, 5.4 eq.) in dichloromethane (200 mL) and 4 Angstrom molecular sieves (35 g) were stirred at ambient temperature for 24 h under nitrogen gas. The reaction mixture was filtered through silica gel 60 to remove copper acetate to give 8.8 g (30% yield) of crude product. Flash chromatography gave product at 40% ethyl acetate in an ethyl acetate/hexane system. The product is an off-white solid (2.0 g, 7% yield). 1H NMR (400 MHz, chloroform-d3) δ ppm 9.64 (s, 1H), 7.43 (m, 2H), 7.28 (s, 1H), 7.31 (s, 1H), 7.11-7.06 (m, 3H), 6.81 (s, 1H), 3.79s (s, 3H); Calc'd for C14H12O4; m/z (M+H+)=245; found 245.

Provenance & Evidence