Phenol → HCID 19099030, compound

HRID 2421872Notes

Reaction equation

HRID 2421872 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[N+:18]([O-:20])=[O:19].CCOC(C)=O>CN(C=O)C>[F:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:12]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 19099030HCID 19099030, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

252 mg of sodium hydride as a 60% suspension in oil (6.29 mmol) are placed in a 50 mL three-necked flask containing 10 mL of DMF and 0.592 g of phenol. The mixture is stirred at room temperature for 1 hour and a solution of 2,6-difluoronitrobenzene 47 (1.0 g, 6.29 mmol) in 10 mL of DMF is added. The reaction medium is left at room temperature for 24 hours. 50 mL of EtOAc are added and the mixture is washed twice with 20 mL of distilled water. The organic phase is dried over MgSO4, filtered and finally evaporated to dryness. The crude product is chromatographed on a silica cartridge (120 g) eluting with heptane/EtOAc (as an EtOAc gradient: 0 to 50%). 1.07 g of expected product 57 are obtained (yellow oil).

Workup

  1. waitThe reaction medium is left at room temperature for 24 hours
  2. washthe mixture is washed twice with 20 mL of distilled water
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customfinally evaporated to dryness
  6. customThe crude product is chromatographed on a silica cartridge (120 g)
  7. washeluting with heptane/EtOAc (as an EtOAc gradient

Sources & evidence

ORD record
ord-fae9aec5014d4be98022b6ba21b16bed
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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