Potassium Carbonate → 1,3-Dimethyl-2-nitro-5-[1-(trifluoromethyl)vinyl]benzene

HRID 874780Notes

Reaction equation

HRID 874780 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[F:13][C:14]([F:21])([F:20])[C:15](B(O)O)=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH3:12][C:4]1[CH:3]=[C:2]([C:15]([C:14]([F:21])([F:20])[F:13])=[CH2:16])[CH:7]=[C:6]([CH3:8])[C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2782677(3,3,3-Trifluoroprop-1-en-2-yl)boronic acidHCID 119589675-Bromo-1,3-dimethyl-2-nitrobenzene

Product 1

HCID 251000761,3-Dimethyl-2-nitro-5-[1-(trifluoromethyl)vinyl]benzeneYield 105.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-bromo-1,3-dimethyl-2-nitrobenzene (10.0 g), [1-(trifluoromethyl)vinyl]boronic acid (purity: 60%, 13.4 g) and potassium carbonate (14.4 g) was dissolved in the mixed solvent of THF and water, which was then degassed three times. To the solution was added dichloro bis(triphenylphosphine)palladium (II) (1.5 g), and the mixture was heated to reflux for 3 hours under argon atmosphere. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 1,3-dimethyl-2-nitro-5-[1-(trifluoromethyl)vinyl]benzene (11.2 g). 1H-NMR (CDCl3) δ: 2.34 (6H, s), 5.78-5.80 (1H, m), 6.03-6.04 (1H, m), 7.20 (2H, s).

Workup

  1. customwas then degassed three times
  2. additionTo the solution was added dichloro bis(triphenylphosphine)palladium (II) (1.5 g)
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 hours under argon atmosphere
  5. additionpoured into water, which
  6. extractionwas then extracted twice with ethyl acetate
  7. washwhich was then washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter the drying agent was filtered off
  10. distillationthe solvent was distilled away under the reduced pressure
  11. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-00c71b5c0d99490389df89743c33366b
Source dataset
uspto-grants-2015_03
Patent number
US08980937B2

Reaction notes

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