Boron tribromide → 8-Chloronaphthalen-2-ol

HRID 1830671Notes

Reaction equation

HRID 1830671 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12]C)[CH:8]=[CH:7]2.B(Br)(Br)Br>>[Cl: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]2

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 220481521-Chloro-7-methoxynaphthalene

Product 1

HCID 215726258-Chloronaphthalen-2-ol

Procedure

The title compound was prepared by reacting 8-chloro-2-methoxynaphthalene (10.25 g, 53.4 mmol) with boron tribromide (67 mL of 1N solution, 67 mmol) according to method D to yield 8.76 g (92%) of a yellow solid. An analytical sample was further purified by reverse phase preparative HPLC to yield the title compound as a white solid: mp 95–100° C.; 1H NMR (DMSO-d6): δ 7.18 (1H, dd, J=2.37 Hz, J=8.85 Hz), 7.23–7.28 (1H, m), 7.41 (1H, d, J=2.28 Hz), 7.59 (1H, d, J=7.37 Hz), 7.81 (1H, d, J=8.15 Hz), 7.87 (1H, d, J=8.86 Hz), 10.17 (1H, s); MS m/z 177/179 (M−H)−.

Sources & evidence

ORD record
ord-8c1c522a6d404e30935e370780dd4ca6
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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