Triphenylphosphine dibromide → 2-(2-Bromoethyl)bicyclo(2.2.1)heptane
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9]O.[Br:11]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:11][CH2:9][CH2:8][CH:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bicylco[2.2.1]hept-2-yl-ethanol (13.0 g, 93 mmol) was dissolved in acetonitrile (200 mL) and treated with dibromotriphenylphosphorane (47.0 g, 0.11 mol). After 1.5 hours the mixture was quenched with water (10 mL), diluted with diethyl ether (400 mL), and washed with water (2×400 mL). The organic phase was dried (MgSO4) and concentrated to yield an oil. The product was passed through a pad of silica gel to yield 2-(2-bromo-ethyl)-bicyclo[2.2.1]heptane as a colorless oil (18 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 3.37 (t, 7.4 Hz, 2 H), 2.22 (m, 1 H), 1.97 (m, 1 H), 1.86 (m, 1 H), 1.7-1.4 (m, 5 H), 1.3-0.9 (m, 5 H); MS (FAB) m/z 203 (MH+).