4-Toluenesulfonyl chloride → 3-(3,5-Difluorophenyl)propyl azide

HRID 1193599Notes

Reaction equation

HRID 1193599 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[F:12][C:13]1[CH:14]=[C:15]([CH2:20][CH2:21][CH2:22]O)[CH:16]=[C:17]([F:19])[CH:18]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>N1C=CC=CC=1.O>[F:12][C:13]1[CH:14]=[C:15]([CH2:20][CH2:21][CH2:22][N:24]=[N+:25]=[N-:26])[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium AzideHCID 140499113-(3,5-Difluorophenyl)propan-1-ol

Product 1

HCID 140499123-(3,5-Difluorophenyl)propyl azideYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Tosyl chloride (0.0814 mol) was added to a cooled (0°) solution of 3-(3,5-difluorophenyl)propanol (0.0407 mol) in pyridine (75 ml). The reaction was stirred 2 hours at 25°, then it was poured into ice/water and extracted into ethyl ether. The ethereal extracts were washed with 3N aqueous hydrogen chloride and water, then were dried over sodium sulfate and concentrated. The residue was dissolved in dimethylformamide (75 ml) and sodium azide (0.0814 mol) was added. The reaction was stirred 8 hours, then was diluted with water and extracted into ethyl acetate. The organic extract was washed with 3N aqueous hydrogen chloride and water, then dried over sodium sulfate and concentrated to yield 6.7 g (64%) of an oily product.

Workup

  1. extractionextracted into ethyl ether
  2. washThe ethereal extracts were washed with 3N aqueous hydrogen chloride and water
  3. dry with materialwere dried over sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dimethylformamide (75 ml)
  6. stirringThe reaction was stirred 8 hours
  7. extractionextracted into ethyl acetate
  8. extractionThe organic extract
  9. washwas washed with 3N aqueous hydrogen chloride and water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e3f679d52e054412be09c1b3352293c2
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

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