Boron tribromide → 1-Chloro-8-fluoro-6-(3-fluoro-4-hydroxyphenyl)-2-naphthol
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)=[C:15]([F:21])[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](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:21])[CH:14]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:22]Participants
3
Procedure
The title compound was prepared by reacting 1-chloro-8-fluoro-6-(3-fluoro-4-methoxyphenyl)-2-naphthol (0.13 g, 0.41 mmol) with boron tribromide (0.8 mL of 1N solution, 0.8 mmol) according to method D to yield 0.070 g (56%) of a white solid mp 198-200° C.; 1H NMR (DMSO-d6): δ 7.03-7.09 (1H, m) 7.34 (1H, d, J=8.92 Hz), 7.49-7.52 (1H, m), 7.68 (2H, d, J=15.0 Hz), 7.85-7.88 (1H, m), 8.02 (1H, d, J=0.70 Hz), 10.13 (1H, s), 10.66 (1H, s); MS (ESI) m/z 305/307 (M−H)−.
Sources & evidence
- ORD record
- ord-05e72d0673774de497c48acbfa636bf2
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06914074B2
Reaction notes
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