Dimethylformamide → 1-(3-Chloropropoxy)-4-fluoro-2-nitrobenzene

HRID 846730Notes

Reaction equation

HRID 846730 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9]O)=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.CN(C)C=O.S(Cl)([Cl:23])=O>ClC(Cl)Cl>[Cl:23][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 150969923-(4-Fluoro-2-nitrophenoxy)propanol

Product 1

HCID 150969711-(3-Chloropropoxy)-4-fluoro-2-nitrobenzeneYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 12.6 parts of 3-(4-fluoro-2-nitrophenoxy)propanol, 0.9 parts of N,N-dimethylformamide and 150 parts of trichloromethane were added dropwise 8.36 parts of thionyl chloride and stirring was continued for 1 hour at room temperature. The whole was further stirred and refluxed for 3 hours. The reaction mixture was evaporated under methylbenzene. The residue was stirred in petroleumether. The product was filtered off and dried, yielding 7.41 parts (55%) of 1-(3-chloropropoxy)-4-fluoro-2-nitrobenzene; mp. 143.3° C. (intermediate 25).

Workup

  1. stirringThe whole was further stirred
  2. temperaturerefluxed for 3 hours
  3. customThe reaction mixture was evaporated under methylbenzene
  4. stirringThe residue was stirred in petroleumether
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-44685fb705fa4fb4b80e711f6f557f29
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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