1-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-one → (1R)-1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

HRID 1499263Notes

Reaction equation

HRID 1499263 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([CH3:14])[CH:3]=1.BrC1C=CC([C@@H](O)C(F)(F)F)=C(N2C=CC(C)=N2)C=1>[Ir]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:13])[C:9]([F:11])([F:12])[F:10])=[C:4]([CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 534028541-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-oneHCID 117942080(R)-1-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol2×

Product 1

HCID 117952721(1R)-1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

Reagents, catalysts & solvents 1

HCID 23924IridiumCatalyst

Procedure

Chiral reduction of 1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanone using the Iridium complex-catalyzed hydrogenation as described for Intermediate 1, (R)-1-(4-bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol provides (R)-1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanol.

Sources & evidence

ORD record
ord-143b9adb11884ca385a9a3a6cc1c635d
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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