Carbon Tetrachloride → 2-(1-Chloroethyl)-5-fluoropyridine

HRID 1694538Notes

Reaction equation

HRID 1694538 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:21].[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH:32](O)[CH3:33])=[N:30][CH:31]=1.CCCCC>C(Cl)Cl>[Cl:21][CH:32]([C:29]1[CH:28]=[CH:27][C:26]([F:25])=[CH:31][N:30]=1)[CH3:33]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8003PentaneHCID 11776TriphenylphosphineHCID 591868831-(5-Fluoropyridin-2-yl)ethan-1-ol

Product 1

HCID 591868842-(1-Chloroethyl)-5-fluoropyridineYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphospine (0.92 g, 3.5 mmol) and CCl4 (4 mL) was stirred for 10 min. and then a solution of 1-(5-fluoropyridin-2-yl)ethanol (0.25 g, 1.7 mmol) in DCM (2 mL) was added. After 18 h, pentane (20 mL) was added, the solid material was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (eluent heptane:ethyl acetate 3:1) affording the title compound (8 mg, 3% yield).

Workup

  1. waitAfter 18 h
  2. customthe solid material was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography (eluent heptane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-af6820bd0fc746cd96180bbe93fcc51e
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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