Potassium Fluoride → HCID 86667306, compound

HRID 2407007Notes

Reaction equation

HRID 2407007 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[F-].[K+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 113333901-Bromo-4-(nitromethyl)benzene

Product 1

HCID 86667306HCID 86667306, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-bromo-4-(nitromethyl)benzene (5.00 g, 20 mmol) in toluene (40 mL) was added palladium tetrakis(triphenylphosphine) (2.67 g, 2.31 mmol), 4-(trifluoromethyl)phenylboronic acid (5.28 g, 27.8 mmol) and potassium fluoride (4.0 g, 69 mmol). The reaction mixture was purged with nitrogen and heated to reflux. Water (10 mL) was added and the mixture was refluxed overnight. The mixture was diluted with saturated aqueous NH4Cl and the phases separated. The aqueous layer was extracted with ethyl acetate (20 mL *3). The combined organic layers were washed with water (50 mL*3), brine, dried over Na2SO4 and concentrated. The crude residue was purified by silica gel chromatography to give 4-(nitromethyl)-4′-(trifluoromethyl)biphenyl (2.0 g) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.66 (m, 6H), 7.57 (d, J=8.0 Hz, 2H), 5.51 (s, 2H).

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. temperatureheated to reflux
  3. additionWater (10 mL) was added
  4. temperaturethe mixture was refluxed overnight
  5. additionThe mixture was diluted with saturated aqueous NH4Cl
  6. customthe phases separated
  7. extractionThe aqueous layer was extracted with ethyl acetate (20 mL *3)
  8. washThe combined organic layers were washed with water (50 mL*3), brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d89c494d3b7b4d50993f05370c6805c8
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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