1-Octanol → Octane, 1-fluoro-

HRID 1283933Notes

Reaction equation

HRID 1283933 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(S(F)(F)[F:16])CC)C.O>C(Cl)Cl>[F:16][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 962WaterHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 10027Octane, 1-fluoro-Yield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.0 g (0.1 mole) of 1-octanol in 25 ml of methylene chloride was added dropwise to a solution of 16.1 g (0.1 mole) of diethylaminosulfur trifluoride in 60 ml methylene chloride cooled to -70° to -65°. The reaction mixture was then warmed to 25° and 50 ml of water was added. The lower organic layer was separated, dried (MgSO4) and then distilled to give 12.0 g (90%) of 1-fluorooctane as a colorless liquid: bp 42°-43° (20 mm), 19F nmr (CCl3F) δ -218.8 ppm (t, t, 1F, J = 49, 25 Hz).

Workup

  1. temperaturecooled to -70° to -65°
  2. temperatureThe reaction mixture was then warmed to 25°
  3. customThe lower organic layer was separated
  4. dry with materialdried (MgSO4)
  5. distillationdistilled

Sources & evidence

ORD record
ord-a2f933d1f8c64ab0a72d1e6737418987
Source dataset
uspto-grants-1976_08
Patent number
US03976691

Reaction notes

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