Dimethylformamide → 1,2-Difluoro-4-methoxy-5-nitrobenzene

HRID 1256021Notes

Reaction equation

HRID 1256021 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CN(C=O)C.IC>O>[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:9][CH3:13])=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27741824,5-Difluoro-2-nitrophenol2×

Product 1

HCID 451081931,2-Difluoro-4-methoxy-5-nitrobenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,5-Difluoro-2-nitrophenol (INTERMEDIATE 51) (2.02 g, 11.54 mmol) and potassium carbonate (2.39 g, 17.3 mmol) were added into a 50 mL round-bottomed flask. DMF (10 mL) was added. Iodomethane (1.08 mL, 17.3 mmol) was added. The reaction mixture was stirred at RT overnight. The mixture was poured into water (60 mL) and stirred for 10 min. Filtration afforded the title product as a precipitate (1.9 g, 87% yield).

Workup

  1. stirringstirred for 10 min
  2. filtrationFiltration

Sources & evidence

ORD record
ord-e861ab369cf9464fbbbf7063492c228c
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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