Triphenylphosphine → HCID 49851937, compound

Participants

Reaction Steps

A solution of alcohol 111 (305 mg, 1.50 mmol) and triphenylphosphine (474 mg, 1.81 mmol) in anhydrous CH2Cl2 (12 mL) was carefully treated with recrystallized N-bromosuccinimide (322 mg, 1.81 mmol) (water bath cooling), and the mixture was stirred at room temperature for 3 h. The resulting solution was concentrated, and then added to excess pentane at the top of a silica gel column (20 g in pentane), rinsing on with minimal extra CH2Cl2. Elution with pentane firstly gave foreruns, and then further elution with 20-50% Et2O/pentane gave 2-[4-(bromomethyl)phenyl]-5-fluoropyridine (112) (348 mg, 87%) as a white solid that was used directly in the next step; 1H NMR (CDCl3) δ 8.54 (d, J=2.9 Hz, 1H), 7.92 (dt, J=8.4, 1.9 Hz, 2H), 7.72 (ddd, J=8.7, 4.3, 0.4 Hz, 1H), 7.52-7.43 (m, 3H), 4.54 (s, 2H); HRESIMS calcd for C12H10BrFN m/z [M+H]+ 267.9955, 265.9975, found 267.9959, 265.9979.

Provenance & Evidence