2-Bromo-6-methoxynaphthalene → 2-Methoxy-6-(3-methoxyphenyl)naphthalene

HRID 895172Notes

Reaction equation

HRID 895172 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:15][CH3:14])[CH:21]=3)[CH:9]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 787862-Bromo-6-methoxynaphthaleneHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 114028342-Methoxy-6-(3-methoxyphenyl)naphthalene

Procedure

The title compound was prepared by reacting 6-methoxy-2-bromonaphthalene (3.09 g, 13.0 mmol) with 3-methoxyphenylboronic acid (2.18 g, 14.3 mmol according to method A to yield 1.18 g (34%) of a white solid: mp 80° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 3.92(3H, s), 6.90 (1H, dd, J=2.17 Hz, J=7.76 Hz), 7.14-7.18 (2H, m), 7.22-7.24 (1H, m), 7.28 (1H, d, J=7.45 Hz), 7.36-7.39, (1H, m), 7.70 (1H, dd, J=1.86 Hz, J=8.70 Hz), 7.77-7.80 (2H, m), 7.96 (1H, d, J=1.24 Hz); MS (ESI) m/z 265 (M+H)+.

Sources & evidence

ORD record
ord-b6090490134741998cf0c40b753ddb00
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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