Furan-2-boronic acid → 4-(Furan-2-yl)-2,6-dimethoxyphenol

Reaction equation

Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O>>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 2734357Furan-2-boronic acid

HCID 148458764-Bromo-2,6-dimethoxyphenol

Product 1

HCID 543508354-(Furan-2-yl)-2,6-dimethoxyphenolYield 79%

Procedure

4-Bromo-2,6-dimethoxyphenol (Lee, H.; et al. Tetrahedron Letters, 2004, 45, 1019) was coupled with 2-furylboronic acid according to the procedure used in the synthesis of Example 21. Purification by chromatography (20-40% EtOAc-hexanes) gave 4-(furan-2-yl)-2,6-dimethoxyphenol as a light orange solid (1.95 g, 79% yield).

Workup

customused in the synthesis of Example 21
customPurification by chromatography (20-40% EtOAc-hexanes)

Sources & evidence

ORD record: ord-5cc3d0ab1b54469587be0918e9e18936
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434707B2

Reaction notes

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