Benzenepropanol → (3-Fluoropropyl)benzene

HRID 450713Notes

Reaction equation

HRID 450713 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]1([CH2:16][CH2:17][CH2:18]O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[F:7][CH2:18][CH2:17][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31234BenzenepropanolHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 11804828(3-Fluoropropyl)benzeneYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

15.6 g of diethylaminosulfurtrifluoride (DAST, 96.91 mmol) were dissolved in 18 ml of dichloromethane. At 0-5° C., 12 g of 3-phenyl-1-propanol (88.1 mmol) dissolved in 30 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 18 h, and, after addition of 30 ml of dichloromethane, poured onto 100 ml of ice water. The organic layer was separated, dried over magnesium sulfate, filtered, and the solvent evaporated. The crude product was purified by distillation at a bath temperature of 106° C. at 20 mm to yield 7.4 g of the title compound.

Workup

  1. additionwere added dropwise
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. distillationThe crude product was purified by distillation at a bath temperature of 106° C. at 20 mm

Sources & evidence

ORD record
ord-7974632c92bd4beb91d4005fbaf92c35
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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