1,3-Dibromopropane → Benzene, 1-[(3-bromopropyl)thio]-4-fluoro-

HRID 2240281Notes

Reaction equation

HRID 2240281 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:9][CH2:10][CH2:11][CH2:12][S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 677894-Fluorothiophenol

Product 1

HCID 14575314Benzene, 1-[(3-bromopropyl)thio]-4-fluoro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Fluorothiophenol (5.3 ml), 1,3-dibromo-propane (15.3 ml), K2CO3 (14 g) were dissolved in CH3CN (100 ml) and refluxed for 3 h. The insoluble salts were removed, the solvent was evaporated and the residue dissolved in ethyl acetate (70 ml). The solution was extracted with diluted NaOH and water, dried and the solvent evaporated in vacuo. The residue was purified by distillation to yield 8 g of the title compound as a colourless oil. Bp. 150-155° C. @ 20 mmHg.

Workup

  1. temperaturerefluxed for 3 h
  2. customThe insoluble salts were removed
  3. customthe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate (70 ml)
  5. extractionThe solution was extracted with diluted NaOH and water
  6. customdried
  7. customthe solvent evaporated in vacuo
  8. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-941bdbb7f5d64135865b0ebb206abcb1
Source dataset
uspto-grants-2010_05
Patent number
US07723360B2

Reaction notes

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