5-Bromofuran-2-carbaldehyde → HCID 86713730, compound

HRID 718028Notes

Reaction equation

HRID 718028 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[F:9][C:10]([C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=1)([F:12])[CH3:11]>O.[Ru](=O)=O>[F:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([C@H:2]2[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][CH2:3]2)=[CH:15][CH:14]=1)([F:12])[CH3:11]

Participants

4

Reactant 2

HCID 6003285-Bromofuran-2-carbaldehydeHCID 468354872-[4-(1,1-Difluoroethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86713730HCID 86713730, compound

Reagents, catalysts & solvents 1

HCID 16211523Ruthenium dioxide hydrateCatalyst

Procedure

The requisite {cis-5-[4-(1,1-difluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of 5-bromofuran-2-carbaldehyde with 2-[4-(1,1-difluoroethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, followed by hydrogenation in the presence of ruthenium(IV) oxide hydrate.

Sources & evidence

ORD record
ord-6aaf6eeea45c4a8e8c2a1ebdb03072a4
Source dataset
uspto-grants-2015_11
Patent number
US09193726B2

Reaction notes

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