Boron tribromide → 2-Fluoro-4-(2-naphthyl)phenol

HRID 1830643Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22048151HCID 22048151, compound

Product 1

HCID 101252242-Fluoro-4-(2-naphthyl)phenol

Procedure

The title compound was prepared by reacting 2-(3-fluoro-4-methoxyphenyl)naphthalene (0.22 g, 0.87 mmol) with boron tribromide (1.75 mL of 1N solution, 1.75 mmol) according to method D to yield 0.13 g (63%) of a white solid: mp 110–112° C.; 1H NMR (DMSO-d6): δ 7.05–7.11 (1H, m), 7.47–7.54 (3H, m), 7.65 (1H, dd, J=2.20 Hz, J=12.92 Hz), 7.82 (1H, dd, J=1.80 Hz, J=8.62), 7.90–7.98 (3H, m), 8.17 (1H, bs), 10.07 (1H, bs); MS (ESI) m/z 237 (M−H)−.

Sources & evidence

ORD record: ord-842ce9669a0e4f1eb3ffaaaa458334c1
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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