Boron tribromide → HCID 10287293, compound

HRID 1830697Notes

Reaction equation

[Br:1][C:2]1[C:3]([OH:22])=[C:4]([Cl:21])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)=[CH:7][C:6]=2[Cl:20].B(Br)(Br)Br>>[Br:1][C:2]1[C:3]([OH:22])=[C:4]([Cl:21])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=1)=[CH:7][C:6]=2[Cl:20]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11176970HCID 11176970, compound

Product 1

HCID 10287293HCID 10287293, compound

Procedure

The title compound was prepared by reacting 3-bromo-1,8-dichloro-6-(4-methoxyphenyl)-2-naphthol (0.18 g, 0.45 mmol) with boron tribromide (0.9 mL of 1N solution, 0.9 mmol) according to method D to yield 0.12 g (69%) of a light brown solid. The product was further purified by reverse phase preparative HPLC to yield the title compound as a white solid: mp 184–188° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.59 Hz), 7.65 (2H, d, J=8.61 Hz), 7.95 (1H, d, J=1.78 Hz), 8.13 (1H, d, J=1.75 Hz), 8.37 (1H, s), 9.74 (1H, s), 10.50 (1H, s); MS (ESI) m/z 381/383/385 (M−H)−.

Sources & evidence

ORD record: ord-d24359e16ab543998c0123c07b442634
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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