Potassium Carbonate → 2,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenyl

HRID 547846Notes

Reaction equation

HRID 547846 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 1009552',4'-Difluoro(1,1'-biphenyl)-4-ol

Product 1

HCID 582877952,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenylYield 63.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromomethyl-3-nitro-benzene (110 mg, 0.508 mmol), 2′,4′-difluoro-biphenyl-4-ol (110 mg, 0.533 mmol), and dried, finely ground potassium carbonate (74 mg, 0.533 mmol) in 10 mL acetone were refluxed under argon for 20 hrs. The reaction mixture was cooled, filtered, concentrated and re-dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated NaHCO3, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography with a gradient of 0-20% ethyl acetate in hexanes to yield 0.11 g (63%) of 2,4-difluoro-4′-(3-nitro-benzyloxy)-biphenyl. LC-MS (ES) calculated for C19H13F2NO3, 341.32; found m/z 340.3 [M−H]−.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionre-dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography with a gradient of 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e0883477654a42e3a7b7fb805db9e4bc
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

Loading…