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

Participants

Role	Name	HCID	Charge
Reactant	Boron tribromide	HCID 25134	—
Reactant	N-[2-[di(propan-2-yl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide;hydrochloride	HCID 9957090	—
Reactant	8-Bromo-7-hydroxy-3-(4-methoxyphenyl)-1-naphthonitrile	HCID 11187337	—
Product	8-Bromo-7-hydroxy-3-(4-hydroxyphenyl)-1-naphthonitrile	HCID 10215342	—

Reaction Steps

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

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06914074B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-074bb627d421422485b877b0a2a1afec
Source note	uspto-grants-2005_07