Boron tribromide → 8-Fluoronaphthalen-2-ol
Reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2Participants
3
Procedure
The title compound was prepared by reacting 1-fluoro-7-methoxynaphthalene (7.99 g, 45.34 mmol) with boron tribromide (68 mL of 1N solution, 68 mmol) according to method D to yield 3.99 g (54%) of a red solid. An analytical sample was prepared by preparative reverse phase HPLC to yield a white solid: mp 89–92° C.; 1H NMR (DMSO-d6): δ 7.16 (1H, dd, J=2.42 Hz, J=8.90 Hz), 7.21–7.25 (3H, m), 7.62–7.65 (1H, m), 7.85 (1H, dd, J=1.72 Hz, J=8.87 Hz), 10.08 (1H, s); MS (ESI) m/z 161 (M−H)−.
Sources & evidence
- ORD record
- ord-2d689ece082d4c3d964934d9e5561af2
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067524B2
Reaction notes
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