Boron tribromide → HCID 59770047, compound

Participants

Reaction Steps

Cool a solution of N-[5-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methoxy-phenyl]-methanesulfonamide (100 mg, 0.247 mmol) in CH2Cl2 (5 mL) to 0° C. Add 23.3□L (62 mg, 0.247 mmol) BBr3 and warm up to room temperature. Stir for 20 min, then add 30.0□L (79.5 mg, 0.317 mmol) more BBr3. Stir at room temperature for 1 h, then dilute reaction with 90 mL saturated aqueous NaHCO3. Stir overnight. Separate the layers, and extract the aqueous layer with CH2Cl2. Combine and dry organics (MgSO4), filter, and concentrate to afford 94 mg (97%) of a white foam, mp 122.6° C. 1H NMR (CDCl3) δ 2.70 (s, 3H), 2.79-3.59 (br m, 4H), 5.94 (s, 1H), 6.39 (s, 1H), 6.70-7.98 (m, 12H); MS (ES) 414 (M+Na), 390 (M−H). HPLC shows 99% purity.

Provenance & Evidence