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

HRID 512637Notes

Reaction equation

HRID 512637 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

3

Reactant 2

HCID 2734357Furan-2-boronic acidHCID 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

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

Sources & evidence

ORD record
ord-cf8f54c0ff5b4eec997a8e34dc25c22f
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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