Boron tribromide → HCID 10171666, compound

HRID 1830647Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=3)=[CH:9][CH:10]=2)[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:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11483494HCID 11483494, compound

Product 1

HCID 10171666HCID 10171666, compound

Procedure

The title compound was prepared by reacting 1-chloro-6-(3-fluoro-4-methoxyphenyl)-2-naphthol (420 mg, 1.39 mmol) with boron tribromide (3.9 mL of 1.0 M solution in CH2Cl2, 3.89 mmol) according to method D to yield 330 mg (82%) of a yellowish solid: mp 195–198° C.; 1H NMR (DMDO-d6): δ 7.08 (1H, t, J=8.86 Hz), 7.32 (1H, d, J=8.89 Hz), 7.47 (1H, dd, J=8.42 Hz, J=1.52 Hz), 7.63 (1H, dd, J=12.88 Hz, J=1.98 Hz), 7.83 (1H, d, J=8.95 Hz), 7.88 (1H, dd, J=8.93 Hz, J=1.61 Hz), 8.05 (1H, d, 8.86 Hz), 8.15 (1H, d, J=1.25 Hz), 10.05 (1H, s), 10.50 (1H, s); MS (ESI) m/z 287/289 (M−H)−.

Sources & evidence

ORD record: ord-698d08cfe6e24a368cb89361fcbb848f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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