Boron tribromide → HCID 10214699, compound

HRID 1830693Notes

Reaction equation

[Cl: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>>[Cl: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 11173646HCID 11173646, compound

Product 1

HCID 10214699HCID 10214699, compound

Procedure

The title compound was prepared by reacting 8-chloro-6-(4-methoxyphenyl)-2-naphthol (0.10 g, 0.35 mmol) with boron tribromide (0.9 mL of 1N solution, 0.9 mmol) according to method D to yield 0.080 g (85%) of product which was further purified by reverse phase preparative HPLC to yield the title compound as a white solid: mp 204–206° C.; 1H NMR (DMSO-d6): δ 6.87 (2H, d, J=8.61 Hz), 7.17 (1H, dd, J=2.34 Hz, J=8.83 Hz), 7.38 (1H, d, J=2.26 Hz), 7.62 (2H, d, J=8.59 Hz), 7.85 (1H, d, J=1.64 Hz), 7.90 (1H, d, J=8.92 Hz), 8.01 (1H, bs), 9.62 (1H, s), 10.14 (1H, s); MS (ESI) m/z 269/(M−H)−.

Sources & evidence

ORD record: ord-e1552537ebaa4361a32465b49edb5842
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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