Acetone → HCID 135574109, compound

Participants

Reaction Conditions

Reaction Steps

Compound 12a (250 mg, 0.74 mmol) was dissolved in 5 mL dry chloroform and chilled to -50° C. using a mixture of dry ice and acetone. To this mixture was added dropwise 7.4 mL of a 1.0 M solution of boron tribromide in dichloromethane. The reaction mixture was allowed to come to room temperature over a period of 4 h. The precipitate was filtered and washed twice with 2 mL portions of ether. This crude product was recrystallized from ethanol to give 13 in 98% yield as white needles; mp >280° C. dec; IR (Nujol) 3326, 1602, 1531; 1H NMR (CD3OD) δ 3.08 (s, 3H), 6.98 (d, 1H, J=8.1), 7.19 (dd, 1H, J=8.1, 1.9), 7.24 (s, 1H), 7.37 (s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 13C NMR (CD3OD) δ 17.8, 109.6, 110.6, 116.1, 117.3, 119.6, 121.2, 122.8, 125.6, 138.4, 142.5, 147.7, 149.5, 152.0, 154.3, 158.3; HRMS calcd for C16H13NO4 : 283.0844; found 283.0839.

Provenance & Evidence