Carbon Tetrachloride → HCID 22106993, compound

HRID 1456600Notes

Reaction equation

HRID 1456600 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7][Cl:34]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 53729251HCID 53729251, compound

Product 1

HCID 22106993HCID 22106993, compoundYield 71.7%

Procedure

4.15 g of 5-fluoro-2-methoxymethoxybenzyl alcohol [prepared as described in step (b) above] were dissolved in 70 ml of tetrahydrof tiran, and then 6.86 g of carbon tetrachloride and 11.69 g of triphenylphosphine were added to the resulting solution, in that order. The resulting mixture was then stirred at room temperature for 1 hour, and then heated under reflux for 5 hours. At the end of this time, insoluble substances were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and purified by silica gel column chromatography, using a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.27 g (yield 71%) of the title compound as an oily substance.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customAt the end of this time, insoluble substances were removed by filtration
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. custompurified by silica gel column chromatography
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e98692b86e3f4441b318acf9103e4830
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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