2-Bromo-6-methoxynaphthalene → 2-Methoxy-6-phenylnaphthalene

HRID 1830620Notes

Reaction equation

HRID 1830620 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:3]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 787862-Bromo-6-methoxynaphthaleneHCID 178418255HCID 178418255, compound

Product 1

HCID 112533082-Methoxy-6-phenylnaphthalene

Procedure

The title compound was prepared by reacting 2-bromo-6-methoxynaphthalene (1.97 g, 8.31 mmol) with phenylmagnesium bromide according to the method used to prepare intermedite 10 to yield 1.59 g (82%) of a white solid: mp 122–126° C.; 1H NMR (CDCl3): δ 3.94 (3H, s), 7.16–7.18 (2H, m), 7.34–7.37 (1H, m), 7.46–7.49 (2H, m), 7.69–7.72 (2H, m), 7.78–7.82 (2H, m), 7.97 (1H, t); MS (El) m/z 234.2 (M)+.

Workup

  1. customto prepare intermedite 10

Sources & evidence

ORD record
ord-22b921d20dc4438e9a443a2d080ffc07
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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