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

HRID 1635670Notes

Reaction equation

[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=2)[N:23]=1>C(#N)C.C(OCC)C>[Br-:20].[Cl:32][C:26]1[CH:25]=[C:24]2[C:29]([CH:30]=[CH:31][C:22]([CH2:21][P+:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:23]2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-9613e2080713438681e179e355a33616
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509476B1

Reaction notes

Loading…