Boron tribromide → 1-Chloro-8-fluoro-6-(4-hydroxyphenyl)-2-naphthol

HRID 1830692Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:21].B(Br)(Br)Br>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11289654HCID 11289654, compound

Product 1

HCID 102862131-Chloro-8-fluoro-6-(4-hydroxyphenyl)-2-naphthol

Procedure

The title compound was prepared by reacting 1-chloro-8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.14 g, 0.46 mmol) with boron tribromide (0.69 mL of 1N solution, 0.69 mmol) according to method D to yield 0.050 g (38%) of a white solid mp 174–176° C.; 1H NMR (DMSO-d6): δ 6.88 (2H, d, J=8.62 Hz), 7.33 (1H, d, J=8.92 Hz), 7.60–7.67 (3H, m), 7.86 (1H, dd, J=1.43 Hz, J=9.02 Hz), 7.95 (1H, d, J=1.37 Hz), 9.68 (1H, s), 10.59 (1H, s); MS (ESI) m/z 287/289 (M−H)−.

Sources & evidence

ORD record: ord-0676b5db4f29421e88d9909fe08dbd77
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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