Boron tribromide → HCID 49850509, compound

Participants

Reaction Conditions

Reaction Steps

Compound 3 (0.23 g, 0.4 mmol) was dissolved in 25 mL of CH2Cl2. The solution was cooled at −78° C. in a dry ice CH2Cl2 bath under argon atmosphere for 1 h. After the solution cooled, 1.0 M boron tribromide (3.28 g, 0.013 mol) dissolved in 25 mL of CH2Cl2 was added dropwise. The reaction mixture was allowed to reach room temperature and was stirred overnight. The solvent was removed and quenched with methanol (30 mL×3). After the methanol was removed, hydrochloric saturated methanol (5 mL) was stirred for 1 h at room temperature. The solution was rotovaped and washed with methanol (30 mL×3) before being extracted in CH2Cl2 with water (50 mL×3). The combined organic layers were evaporated and a dissolved in a minimum volume and purified by silica gel TLC plate that was developed in 3% methanolic NH3 (7 M NH3 in methanol)/97% CH2Cl2. The product was obtained as pale yellow oil (68.31%). 1H NMR (CDCl3) δ 8.562 (d, 1H, Ar), 7.652 (ddd, 1H, Ar), 7.280 (m, 3H, Ar), 7.220 (d, 2H, Ar), 7.161 (m, 3H, Ar), 6.980 (d, 1H, Ar), 6.823 (d, 1H, Ar), 6.755 (ddd, 1H, Ar), 3.790 (s, 2H, —CH2—), 3.757 (s, 2H, —CH2—), 3.168 (d, 2H, —CH2—), 2.544 (m, 3H, —CH—CH2—), 2.458 (t, 2H, —CH2—), 2.225 (t, 2H, —CH2—), 2.016 (m, 2H, —CH2—), 1.858 (d, 2H, —CH2—), 1.569 (m, 4H, —CH2—CH2—), 1.236 (m, 4H, —CH2—CH2—). Mass Spec.=458.32 (M+H)+.

Provenance & Evidence