Methanol → 1-Fluoro-3-methoxy-2-nitrobenzene

HRID 2421868Notes

Reaction equation

HRID 2421868 reaction equation
[H-].[Na+].CO.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](F)[C:7]=1[N+:13]([O-:15])=[O:14].C[CH2:17][O:18]C(C)=O>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:18][CH3:17])[C:7]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 27827761-Fluoro-3-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

252 mg of sodium hydride as a 60% suspension in oil (6.29 mmol) are placed in a 100 mL three-necked flask containing 10 mL of THF and 0.255 mL of MeOH. 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 THF is added. The reaction medium is left at room temperature for 16 hours. 10 mL of EtOAc are added and the resulting mixture is washed twice with 20 mL of distilled water. The organic phase is dried over MgSO4, filtered and finally evaporated to dryness. 0.93 g of product 52 is obtained (cream-coloured solid).

Workup

  1. waitThe reaction medium is left at room temperature for 16 hours
  2. washthe resulting 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

Sources & evidence

ORD record
ord-d602463d85cf4061bc531776c59ef8de
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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