1-Fluoro-3-nitrobenzene → HCID 20565505, compound

HRID 848514Notes

Reaction equation

HRID 848514 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH3:16])[CH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9].F[C:18]1[CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>CS(C)=O>[CH3:16][N:5]([CH3:4])[CH2:6][CH2:7][CH:8]([O:9][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 2770479AC1MCIJF

Product 1

HCID 20565505HCID 20565505, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

57 ml of dimethylsulfoxide were added at 60°-65° C. to 5.7 g of a 50% oil-sodium hydride suspension and after cooling the mixture to 25° C., 10.55 g of N,N-dimethyl-3-phenyl-3-hydroxy-propanamine hydrochloride were added thereto under an inert atmosphere. The mixture stood at room temperature and 10.6 ml of 3-fluoro-nitrobenzene were added thereto. After standing at 25° C. for 18 hours, the mixture was extracted with methylene chloride and the organic phase was washed with water and evaporated to dryness under reduced pressure to obtain 25 g of raw product. The latter was extracted twice with 50 ml of N hydrochloric acid and the neutral fraction was extracted twice with 100 ml of ether. The aqueous phase was made alkaline with an excess of sodium hydroxide solution and was extracted with methylene chloride. The organic phase was washed with water and evaporated to dryness under reduced pressure to obtain 11 g of N,N-dimethyl-γ-(3-nitrophenoxy)-benzene-propanamine.

Workup

  1. customstood at room temperature
  2. extractionthe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with water
  4. customevaporated to dryness under reduced pressure
  5. customto obtain 25 g of raw product
  6. extractionThe latter was extracted twice with 50 ml of N hydrochloric acid
  7. extractionthe neutral fraction was extracted twice with 100 ml of ether
  8. extractionwas extracted with methylene chloride
  9. washThe organic phase was washed with water
  10. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-196c9478383140719bac443f84a75caf
Source dataset
uspto-grants-1981_10
Patent number
US04296126

Reaction notes

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