Boron tribromide → HCID 10149584, compound

HRID 1830696Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:9][C:10]=2[Cl:12])[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:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:9][C:10]=2[Cl:12])[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 11186232HCID 11186232, compound

Product 1

HCID 10149584HCID 10149584, compound

Procedure

The title compound was prepared by reacting 1,8-dichloro-6-(4-methoxyphenyl)-2-naphthol (0.12 g, 0.38 mmol) with boron tribromide (0.75 mL of 1N solution, 0.75 mmol) according to method D to yield 0.10 (86%) of which was further purified by reverse phase preparative HPLC to yield the title compound as a white solid: mp 172–174° C. (dec.); 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.54 Hz), 7.36 (1H, d, J=8.90 Hz), 7.65 (2H, d, J=8.56 Hz), 7.88–7.91 (2H, m), 8.10 (1H, d, J=1.63 Hz), 9.69 (1H, s), 10.64 (1H, s); MS (ESI m/z 303/305/307 (M−H)−. Anal. for C16H10Cl2O2.0.25 H2O Calc'd: C,62.98 H, 3.30 Found: C,61.80 H, 3.08

Sources & evidence

ORD record: ord-263a9b7274bc4d9fb0a1355d86187d77
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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