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

HRID 419263Notes

Reaction equation

HRID 419263 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.[Na+].[Na+].C(C#N)(C)=O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.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 10340Sodium CarbonateHCID 694302-OxopropiononitrileHCID 27339503-Tolylboronic acidHCID 112190241-(4-Bromophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 666492512,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanolYield 79%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

Alternatively, 1-(4-bromophenyl)-2,2,2-trifluoroethanol (0.98 g, 3.86 mmol), m-tolylboronic acid (0.63 g, 4.63 mmol), Pd(PPh3)2Cl2 (0.16 g, 0.232 mmol Pd), Na2CO3 (0.90 g, 8.49 mmol), AcCN (10 mls), and H2O (10 mls) were combined and heated in the microwave at 150° C. for 10 minutes. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, concentrated, slurried in CH2Cl2, filtered, and chromatographed over silica gel (CH2Cl2) to give 0.80 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 79%.

Workup

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

Sources & evidence

ORD record
ord-e6ba2371cb7c4441ba00662923c63263
Source dataset
uspto-grants-2012_01
Patent number
US08093291B2

Reaction notes

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