Potassium Fluoride → 2,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenyl

HRID 642802Notes

Reaction equation

HRID 642802 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.[F-].[K+]>C1(C)C=CC=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

5

Reactant 3

HCID 522689Potassium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 70220962-Bromo-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 674856592,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenylYield 53.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-1,3-dimethyl-5-nitro-benzene (1 g, 4.3 mmol) in toluene (20 mL) is added palladium tetrakis triphenylphosphine (0.5 g, 0.43 mmol), 4-trifluoromethyl phenyl boronic acid (1.65 g, 8.7 mmol), and potassium fluoride (0.75 g, 12.9 mmol). The reaction is purged with nitrogen three times and heated to reflux under nitrogen. At the reflux temperature, water (5 mL) is added to the reaction and the reaction is allowed to reflux under nitrogen. The reaction is monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction is diluted with ethyl acetate and Celite® is added, followed by water. This mixture is then filtered through a pad of Celite®. The solution is poured into a separatory funnel and the organic layer is washed with water and brine. The organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified by flash column chromatography eluting with ethyl acetate/hexanes to afford 0.68 g of the titled compound as a yellow solid. 1H-NMR.

Workup

  1. customThe reaction is purged with nitrogen three times
  2. temperatureheated
  3. temperatureto reflux under nitrogen
  4. additionAt the reflux temperature, water (5 mL) is added to the reaction
  5. temperatureto reflux under nitrogen
  6. additionThe reaction is diluted with ethyl acetate and Celite®
  7. additionis added
  8. filtrationThis mixture is then filtered through a pad of Celite®
  9. additionThe solution is poured into a separatory funnel
  10. washthe organic layer is washed with water and brine
  11. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue is purified by flash column chromatography
  14. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-54b0c1974b2e43cd9cbb4067b1650e28
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

Loading…