Phosphorus tribromide → 3-Bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[CH2:22]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:25]>C(OCC)C>[Br:25][CH2:22][C:9]1[N:10]([CH:19]([CH3:21])[CH3:20])[C:11](=[O:18])[C:12]2[C:17]([C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-(4-fluorophenyl)-3-hydroxymethyl-2-isopropyl-1-oxo-1,2-dihydroisoquinoline [5.0 g; prepared as described in Reference Example 2(e)] in diethyl ether (200 ml) was treated with phosphorus tribromide (2.0 ml). The resulting mixture was stirred and heated at reflux for 90 minutes, and then cooled and diluted with diethyl ether (200 ml). The solution was washed with water (3×50 ml), dried over magnesium sulphate, and evaporated to dryness, to give 3-bromomethyl-4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline in the form of a white solid (5.8 g), m.p. 116°-119° C.