Boron tribromide → 8-Fluoro-6-(4-hydroxy-phenyl)-naphthalen-2-ol

HRID 1830679Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11311694HCID 11311694, compound

Product 1

HCID 103080908-Fluoro-6-(4-hydroxy-phenyl)-naphthalen-2-ol

Procedure

The title compound was prepared by reacting 8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.10 g, 0.37 mmol) with boron tribromide (0.56 mL of 1N solution, 0.56 mmol) according to method D to yield 0.10 g (quantitative) of a white solid: mp 236–238° C.; 1H NMR (DMSO-d6): δ 6.87 (2H, d, J=8.57 Hz), 7.14–7.18 (2H, m), 7.52 (1H, dd, J=1.18 Hz, J=12.78 Hz), 7.61 (2H, d, J=8.59 Hz, 7.86–7.89 (2H, m), 9.61 (1H, bs), 10.05 (1H, bs); MS (ESI) m/z 253 (M−H)−.

Workup

customto yield 0.10 g (quantitative) of a white solid

Sources & evidence

ORD record: ord-5dbc11805b8245af93ea9a408c39251c
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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