(3-Methoxyphenyl)boronic acid → 2-Methoxy-7-(3-methoxyphenyl)naphthalene

HRID 1830612Notes

Reaction equation

HRID 1830612 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>>[CH3:18][O:17][C:11]1[CH:12]=[CH:13][C:14]2[C:9](=[CH:8][C:7]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:22][CH3:21])[CH:28]=3)=[CH:16][CH:15]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl ester

Product 1

HCID 114484492-Methoxy-7-(3-methoxyphenyl)naphthalene

Procedure

The title compound was prepared by reacting 7-methoxy-2-naphthyl trifluoromethanesulfonate (2.20 g, 7.18 mmol) with 3-methoxyphenylboronic acid (1.20 g, 7.90 (mmol) according to method A above to yield a white solid: mp 58–59° C.; 1H NMR (CDCl3): δ 3.89 (3H, s), 3.93 (3H, s), 6.91–6.94 (1H, m), 7.15 (1H, dd, J=2.42 Hz, J=8.83 Hz), 7.19 1H, d, J=2.27 Hz), 7.23–7.25 (1H, m), 7.28–7.31 (1H, m), 7.37–7.42 (1H, m), 7.59 (1H, dd, J=1.56 Hz, J=8.46 Hz), 7.75 (1H, d, J=8.84 Hz), 7.83 (1H, d, J=8.45 Hz), 7.94 (s1H, s); MS (ESI) m/z 265 (M+H)−.

Workup

  1. customto yield a white solid

Sources & evidence

ORD record
ord-8c198b8dddb24eae808842b6b673bddd
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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