Triphenylphosphine → ((7-Chloroquinolin-2-yl)methyl)triphenylphosphonium bromide

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (1.83 g, 6.99 mmol) was added portionwise to a magnetically stirred solution of 2-bromomethyl-7-chloroquinoline (1.2 g, 4.69 mmol) in dry acetonitrile (10.0 ml) at 60° C. The resulting yellow solution was heated at 60° C. for 27 h with the precipitation of a cream solid. The cooled solution was diluted with diethyl ether (8.0 ml) and filtered to afford the title compound as a cream solid (1.95 g, 80%). Crystallised from ethanol and ethyl acetate as a cream microcrystalline solid, m.p. >200° C.; (Found: C, 64.61; H, 4.22; N, 2.62; Cl, 6.82. C28H22ClBrNP requires C, 64.82; H, 4.27; N, 2.70, Cl, 6.83%). νmax (nujol)/cm-1 1610.0, 1594.0. δH (270 MHz) 5.94 (2H, d, CH2P, 3J=14.2 Hz); 7.43 (1H, dd, 6-H, Jo =8.6, Jm =2.0 Hz); 7.50 (1H, d, 8-H, Jm =2.0 Hz); 7.57-7.95 (16H, m, ArH); 8.03 (1H, d, 3-H, Jo =8.6 Hz); 8.11 (1H, d, 4-H, Jo =8.6 Hz); m/z 437.4 (1.18), 262.3 (11.01), 177.1 (3.13), 43.1 (100).

Provenance & Evidence