Boron tribromide → 8-Bromo-7-hydroxy-3-(4-hydroxyphenyl)-1-naphthonitrile

HRID 895254Notes

Reaction equation

HRID 895254 reaction equation
[Br:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]#[N:13])=[CH:9][C:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)=[CH:7]2.B(Br)(Br)Br.CC(N(C(C)C)CCNC(C1N=C(NC(C2C(O)=CC(OC)=C(OC)C=2)=O)SC=1)=O)C.Cl>>[Br:1][C:2]1[C:3]([OH:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]#[N:13])=[CH:9][C:8]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[CH:7]2

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 9957090N-[2-[di(propan-2-yl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide;hydrochlorideHCID 111873378-Bromo-7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile

Product 1

HCID 102153428-Bromo-7-hydroxy-3-(4-hydroxyphenyl)-1-naphthonitrile

Procedure

The title compound was prepared by reacting 8-bromo-7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile (0.13 g, 0.37 mmol) with boron tribromide (1.1 mL of 1 N solution, 1.1 mmol) according to method D to yield 0.050 g (40%) of an off white solid: mp 204-208° C.(d); 1H NMR (DMSO-d6): δ 6.90 (2H, d, J=8.30 Hz), 7.41 (1H, d, J=8.79 Hz), 7.72 (2H, d, J=8.79 Hz), 8.02 (1H, d, J=9.23 Hz), 8.37 (1H, d, J=1.95 Hz), 8.47 (1H, d, J=2.44 Hz), 9.72 (1H, s), 11.16 (1H, s); MS (ESI) m/z338/340 (M−H).Anal. for C17H10BrNO2

Workup

  1. customto yield 0.050 g (40%) of an off white solid

Sources & evidence

ORD record
ord-074bb627d421422485b877b0a2a1afec
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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