Dimethylformamide → 4-Fluoro-2-nitro-1-propoxybenzene

HRID 2388098Notes

Reaction equation

HRID 2388098 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].I[CH2:13][CH2:14][CH3:15].[F:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1>O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:13][CH2:14][CH3:15])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 1362364-Fluoro-2-nitrophenol

Product 1

HCID 669171744-Fluoro-2-nitro-1-propoxybenzeneYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A N,N-dimethylformamide (DMF) solution (3 ml) of potassium carbonate (3.48 g, 25.2 mmol) and 1-iodopropane (3.95 g, 23.2 mmol) was added to a DMF solution (7 ml) of 4-fluoro-2-nitrophenol (3.3 g, 21.0 mmol). The mixture was stirred at room temperature for 48 hours. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution twice, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=9:1). The purified product was concentrated under reduced pressure to thereby obtain 4.03 g of oily yellow 4-fluoro-2-nitro-1-propoxybenzene (yield: 96%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution twice
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcc4de1a4f674fc6bb15a6f74ad2fb11
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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