Phosphorus tribromide → 10-Bromomethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline
Reaction equation
O[CH2:2][C:3]1[C:4]2[CH2:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[NH:8][C:7]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1.P(Br)(Br)[Br:22]>C1COCC1>[Br:22][CH2:2][C:3]1[C:4]2[CH2:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[NH:8][C:7]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1Participants
4
Procedure
Fine powder of Compound (I)(25) (10-hydroxymethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline, 7.3 g, 27.7 mmol) was suspended in THF (150 mL). A solution of PBr3 (83 mL, 1M in dichloromethane) was added dropwise at room temperature. After the complete addition, the resultant mixture was stirred overnight and quenched by addition of water (150 mL). The suspension was stirred for 1 hour and filtered. The resultant solid was washed with water (2×100 mL) and ethyl acetate (2×100 mL) and dried in a vacuum oven to provide 10-Bromomethyl-5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline in 81% yield. 1H NMR spectrum (in DMSO-d6): δ 12.31 (s, 1H); 8.23 d, J=7.5 Hz, 1H); 7.95 (m, 1H); 7.75 (m, 2H); 7.45 (m, 2H); 4.87 (s, 2H); 3.97 (s, 2H).