5-Formylfuran-2-boronic acid → 1-Bromo-4-(pentafluoroethyl)benzene

HRID 718027Notes

Reaction equation

HRID 718027 reaction equation
[CH:1]([C:3]1[O:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1>[Pd]>[F:23][C:18]([F:24])([C:15]1[CH:14]=[CH:13][C:12]([C@H:6]2[O:7][C@@H:3]([CH2:1][OH:2])[CH2:4][CH2:5]2)=[CH:17][CH:16]=1)[C:19]([F:20])([F:22])[F:21].[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:23])([F:24])[C:19]([F:20])([F:21])[F:22])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 27343555-Formylfuran-2-boronic acidHCID 542097081-Bromo-4-(pentafluoroethyl)benzene

Product 2

HCID 542097081-Bromo-4-(pentafluoroethyl)benzeneHCID 86713729{cis-5-[4-(Pentafluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The requisite {cis-5-[4-(pentafluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of (5-formylfuran-2-yl)boronic acid with 1-bromo-4-(pentafluoroethyl)benzene, followed by hydrogenation over palladium on carbon. 1-Bromo-4-(pentafluoroethyl)benzene was prepared according to the method of W. Lambert et al., PCT Int. Appl., 2011017513, Feb. 10, 2011.

Sources & evidence

ORD record
ord-d3e81d7f2a9241e2acb738957e629d14
Source dataset
uspto-grants-2015_11
Patent number
US09193726B2

Reaction notes

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