Boron tribromide → HCID 10236706, compound

HRID 895250Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:21])[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:22].B(Br)(Br)Br>>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:21])[C:8]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:22]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22048149HCID 22048149, compound

Product 1

HCID 10236706HCID 10236706, compound

Procedure

The title compound was prepared by reacting 1,5-dichloro-8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.15 g, 0.445 mmol) with boron tribromide (0.67 mL of 1 N solution, 0.67 mmol) according to method D to yield 0.12 g (83%) of a light yellow solid mp 206-216° C.; 1H NMR (DMSO-d6): δ 6.88 (2H, d, J=8.55 Hz), 7.34-7.39 (3H, m), 7.51 (1H, d, J=9.34 Hz), 8.21 (1H, dd, J=1.66 Hz, J=9.34 Hz), 9.74 (1H, bs), 10.99 (1H, bs); MS (ESI) m/z321/323/326 (M−H)−.

Sources & evidence

ORD record: ord-afe6e357ee9a4539ae26fead0b2beb21
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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