Hydrochloric Acid → HCID 58189127, compound

Participants

Reaction Conditions

Reaction Steps

Into a 25 mL flame-dried flask were added diethylzinc (8.75 mL, 1 N solution in hexanes). The solution was cooled to −20° C. and a solution of trichloroacetic acid (1.43 g, 8.75 mmol, dissolved in 2 mL of CH2Cl2 was added dropwise over 10 min, then the solution was stirred an additional 20 min. A solution of diiodomethane (2.38 g, 8.89 mmol) in 1 mL CH2Cl2 was then added dropwise and the solution was stirred an additional 20 minutes. A solution of 4-bromo-1-methoxy-2-vinyloxy-benzene (1.029 g, 4.365 mmol, dissolved in 900 uL CH2Cl2) was then added and the reaction mixture was stirred for 8 h at room temperature. The reaction mixture was poured onto a 100 mL 1 N aqueous HCl solution containing some ice, then extracted 3× with EtOAc. The combined organic phase was washed with 1 N aqueous NaHCO3, brine, then dried (MgSO4), filtered and concentrated. Purification by flash column on silica gel (0-100% Hexanes/EtOAc gradient) to afford titled compound as a colorless crystalline solid (738 mg, 67%). 1H NMR (DMSO-d6) 7.33 (s, 1H), 7.06 (d, J=8.4, 1H), 6.90 (d, J=8.4, 1H), 3.84 (m, 1H), 3.70 (s, 3H), 0.75 (m, 2H), 0.64 (m, 2H). LC/MS (Method B) 3.64 min, [M+1]+ 243/245.

Provenance & Evidence