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

HRID 469887Notes

Reaction equation

HRID 469887 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-1b92af23aab94e7c8cda94b86c4689df
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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