Methyl 7-bromo-3-methoxy-2-naphthoate → 3-Methoxy-7-(3-methoxyphenyl)-2-naphthoic acid methyl ester

HRID 1035607Notes

Reaction equation

HRID 1035607 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[CH3:18][O:19][C:20]1[CH:21]=[C:22](OB(O)O)[CH:23]=[CH:24][CH:25]=1>>[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([O:19][CH3:18])[CH:25]=3)=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 14528105Methyl 7-bromo-3-methoxy-2-naphthoateHCID 221738233-Methoxyphenylboric acid

Product 1

HCID 594434733-Methoxy-7-(3-methoxyphenyl)-2-naphthoic acid methyl esterYield 66%

Procedure

The compound is prepared by the reaction of 7-bromo-3-methoxy-2-naphthoic acid methyl ester (2.2 g, 7.45 mmol, 1 eq) with 3-methoxyphenylboric acid (1.37 g, 8.95 mmol, 1.5 eq) according to method A. Purification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 66%, 1.58 g.

Workup

  1. customPurification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent

Sources & evidence

ORD record
ord-33054ef7613f4cc2bdcd48b397cd1685
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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