N-bromobutanimide → 8-Bromo-7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

HRID 895245Notes

Reaction equation

HRID 895245 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=[C:9]2[C:12]#[N:13])=[CH:4][CH:3]=1.C1C(=O)N([Br:29])C(=O)C1>C1COCC1>[Br:29][C:11]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[C:9]([C:12]#[N:13])=[CH:8][C:7]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[CH:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 112543667-Hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

Product 1

HCID 111873378-Bromo-7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile (0.160 g, 0.58 mmol) with NBS (0.12 g, 0.70 mmol) in THF (10 mL) according to method C to yield 0.080 g (39%) of a yellow solid: mp 145-146° C.; 1H NMR (DMSO-d6): δ 3.83 (3H, s), 7.08 (2H, d, J=8.79 Hz), 7.42 (1H, d, J=8.79 Hz), 7.84 (2H, d, J=8.79 Hz), 8.04 (1H, d, J=8.79 Hz), 8.42 (1H, d, J=1.95 Hz), 8.53 (1H, d, J=1.95 Hz), 11.21 (1H, s); MS (ESI) m/z 354/356 (M+H+; MS (ESI) m/z 352/354 (M−H)−.

Sources & evidence

ORD record
ord-73371387546c4dd08f8cea001f1e61e5
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

Loading…