Furan-2-boronic acid → 2-(4-(Difluoromethoxy)-3,5-dimethoxyphenyl)furan

HRID 512645Notes

Reaction equation

HRID 512645 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:10][CH:11]([F:13])[F:12])=[C:6]([O:8][CH3:9])[CH:7]=1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O>>[F:12][CH:11]([F:13])[O:10][C:5]1[C:4]([O:14][CH3:15])=[CH:3][C:2]([C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)=[CH:7][C:6]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 2734357Furan-2-boronic acidHCID 584320715-Bromo-2-(difluoromethoxy)-1,3-dimethoxybenzene

Product 1

HCID 584320532-(4-(Difluoromethoxy)-3,5-dimethoxyphenyl)furan

Procedure

5-Bromo-2-(difluoromethoxy)-1,3-dimethoxybenzene was coupled with 2-furylboronic acid following the procedure for the synthesis of Example 21. Purification by chromatography (0-30% EtOAc-hexanes) provided 2-(4-(difluoromethoxy)-3,5-dimethoxyphenyl)furan as a white crystalline material (0.555 g, 67% yield).

Workup

  1. customfor the synthesis of Example 21
  2. customPurification by chromatography (0-30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-590e96431fd14597b54eb36d4197b59f
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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