4-(Trifluoromethyl)phenylboronic acid → 2,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenyl

HRID 2173797Notes

Reaction equation

HRID 2173797 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.O.[F-].[K+]>C1(C)C=CC=CC=1.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>[CH3:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[C:7]([CH3:8])[C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 70220962-Bromo-1,3-dimethyl-5-nitrobenzeneHCID 23675105Potassium fluoride hydrate

Product 1

HCID 674856592,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenylYield 43.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-1,3-dimethyl-5-nitrobenzene (2.7 g, 11.7 mmol) in toluene (36 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.36 g, 1.17 mmol), 4-(trifluoromethyl)phenylboronic acid (4.46 g, 23.5 mmol), and potassium fluoride hydrate (3.31 g, 43 mmol). The reaction was purged with nitrogen three times. Water (9 mL) was added and the reaction was refluxed overnight. The reaction was diluted with saturated ammonium chloride and the layers were separated. The organic layer was washed with water (3×40 mL) and brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 2,6-dimethyl-4-nitro-4′-(trifluoromethyl)biphenyl (1.5 g, 43%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 7.99 (s, 2H), 7.75 (d, 2H), 7.26 (s, 1H), 7.25 (s, 1H), 2.10 (s, 6H).

Workup

  1. customThe reaction was purged with nitrogen three times
  2. additionWater (9 mL) was added
  3. temperaturethe reaction was refluxed overnight
  4. additionThe reaction was diluted with saturated ammonium chloride
  5. customthe layers were separated
  6. washThe organic layer was washed with water (3×40 mL) and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by column chromatography

Sources & evidence

ORD record
ord-58cee13e4f6843d287259b3071ce736e
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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