Phenylboronic Acid → 5,6-Dimethoxybiphenyl-3-carboxylic acid

HRID 638955Notes

Reaction equation

HRID 638955 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[C:14]([OH:16])=[O:15]>>[CH3:23][O:22][C:18]1[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[CH:12]=[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:19]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 2304593-Iodo-4,5-dimethoxybenzoic acid

Product 1

HCID 686852095,6-Dimethoxybiphenyl-3-carboxylic acidYield 88%

Procedure

5,6-Dimethoxybiphenyl-3-carboxylic acid was prepared by coupling phenylboronic acid with 3-iodo-4,5-dimethoxybenzoic acid according to Method P. The crude product was purified via flash column chromatography on silica gel (5% MeOH in CH2Cl2 as an eluent) to give the desired acid in 88% yield. ESMS: m/z 257.3 [M−H].

Workup

  1. customThe crude product was purified via flash column chromatography on silica gel (5% MeOH in CH2Cl2 as an eluent)

Sources & evidence

ORD record
ord-2695f8d50e7f419586a0f61c2dc40278
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

Loading…