Ethanol → 2,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol

HRID 254783Notes

Reaction equation

HRID 254783 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C([O-])([O-])=O.[K+].[K+].CCO>[Pd].C(Cl)Cl.O>[F:10][C:9]([F:12])([F:11])[CH:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH3:23])[CH:15]=1)[OH:13]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 27339503-Tolylboronic acidHCID 112190241-(4-Bromophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 666492512,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanolYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Bromophenyl)-2,2,2-trifluoroethanol (0.13 g, 0.525 mmol), m-tolylboronic acid (0.1 g, 0.736 mmol), Fibercat (4.28% Pd, 47 mgs, 0.0157 mmol Pd), K2CO3 (0.22 g, 1.576 mmol), EtOH (3 mls), and H2O (0.5 mls) were combined and heated at 80° C. for 4 hours. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, filtered, concentrated, slurried in CH2Cl2, and chromatographed over silica gel (CH2Cl2) to give 0.1 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 72%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customchromatographed over silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-5d05271ca8e549d09a512f7dbdb17405
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

Loading…