Carbon tetrabromide → HCID 57544367, compound

Participants

Reaction Steps

A solution of triphenylphosphine (469 mg, 1.79 mmol) in dry CH2Cl2 (2 mL) was added dropwise to a stirred solution of carbon tetrabromide (592 mg, 1.79 mmol) and (3-iodo-2-naphthyl)methanol (423 mg, 1.49 mmol) in dry CH2Cl2 (11 mL) at room temperature under N2. The reaction was stirred for 4 h at room temperature and was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-50% EtOAc in hexanes gradient) to afford 2-(bromomethyl)-3-iodonaphthalene, as a colorless solid. Rf=0.84 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 8.39 (s, 1H); 7.94 (s, 1H); 7.78-7.76 (m, 1H); 7.71-7.69 (m, 1H); 7.52-7.48 (m, 2H); 4.76 (s, 2H).

Provenance & Evidence