Boron tribromide → 1-Fluoro-6-(4-hydroxy-phenyl)-naphthalen-2-ol
Reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[F:21].B(Br)(Br)Br>>[F:21][C:4]1[C:5]2[C:10](=[CH:9][C:8]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[OH:2]Participants
3
Procedure
The title compound was prepared by reacting 2-methoxy-6-(4-methoxyphenyl)-1-fluoronaphthalene (0.250 g, 0.886 mmol) with boron tribromide (2.7 mL of 1 N solution, 2.7 mmol) according to method D to yield 0.13 g (15%) of a white solid: mp 219–224° C.; 1H NMR (DMSO-d6): δ (6.89 (2H, d, J=8.49 Hz), 7.22–7.28 (1H, m), 7.61 (2H, d, J=8.53 Hz), 7.65 (1H, d, J=9.12 Hz), 7.79 (1H, d, J=8.77 Hz), 7.92 (1H, d, J=8.73 Hz), 8.05 (1H, s), 9.63 (1H, bs), 10.00 (1H, bs); MS (ESI) m/z 253 (M−H)−.
Sources & evidence
- ORD record
- ord-36a72de3bce64cf6b390e1c2aac18b76
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067524B2
Reaction notes
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