p-Fluoronitrobenzene → 1-(3-Chloropropoxy)-4-nitrobenzene

HRID 1030273Notes

Reaction equation

HRID 1030273 reaction equation
CC([O-])(C)C.[K+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Cl:17][CH2:18][CH2:19][CH2:20][OH:21]>CS(C)=O>[Cl:17][CH2:18][CH2:19][CH2:20][O:21][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 123133-Chloro-1-propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 118446171-(3-Chloropropoxy)-4-nitrobenzeneYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a cooled (5°-10° C.) suspension of KOtBu (1.34 g, 11.96 mmol) in DMSO (5 mL) was added a solution of 4-fluoronitrobenzene (1.61 g, 11.39 mmol) and 3-chloro-1-propanol (1.13 g, 11.96 mmol) in DMSO (5 mL). The cooling bath was removed and stirring was continued for 3 hours. The mixture was diluted with water (100 mL) and extracted with ether. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give a brown oil. Purification by flash chromatography (10% EtOAc/hexane) gave 850 mg (35%) of product as a yellow oil.

Workup

  1. temperatureTo a cooled
  2. customThe cooling bath was removed
  3. additionThe mixture was diluted with water (100 mL)
  4. extractionextracted with ether
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customPurification by flash chromatography (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-4090af42055b44869cdcf96f3df7d6d5
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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