Phenol → HCID 68487133, compound

HRID 1875052Notes

Reaction equation

HRID 1875052 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13](F)[C:12]=1[F:21]>C1COCC1>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:12]=1[F:21]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 68487133HCID 68487133, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% oil dispersion) (2.125 g, 53.1 mmol) was added in portions to a solution of phenol (5.00 g, 53.1 mmol) in THF (100 mL) while cooling in an ice bath. After 30 min, 1,2,3-trifluoro-4-nitrobenzene (6.11 mL, 53.1 mmol) was added. The mixture was stirred at RT overnight. The reaction mixture was poured on to ice/10% aqueous HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated. Chromatography of the residue (ethyl acetate:hexane) gave the crude product (10.78 g, 43%) as a yellow oil.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3e10a8dbd68845f098a73c24b365621c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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