Potassium Carbonate → HCID 67981173, compound

HRID 2173788Notes

Reaction equation

HRID 2173788 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:10][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([C:12]([F:23])([F:22])[F:11])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 67981173HCID 67981173, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-3-methylbenzonitrile (1.00 g, 5.10 mmol), 4-(trifluoromethyl)phenylboronic acid (0.969 g, 5.10 mmol), potassium carbonate (1.76 g, 12.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.295 g, 0.255 mmol) in 1:1 dioxane:water (20 mL) was stirred at 80° C. overnight. The mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 2-methyl-4′-(trifluoromethyl)biphenyl-4-carbonitrile (1.26 g, 95%). 1H NMR (400 MHz, CDCl3, δ): 7.72 (d, 2H), 7.59 (s, 1H), 7.56 (d, 1H), 7.42 (d, 2H), 7.31 (d, 1H), 2.29 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-808947603c694b788b437c454b76c6d1
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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