Carbon Tetrachloride → alpha,alpha'-Dichloro-2,5-difluoro-para-xylene

HRID 1391074Notes

Reaction equation

HRID 1391074 reaction equation
C(N(CC)CC)C.P(Cl)(Cl)(Cl)(Cl)Cl.P(Cl)(Cl)([Cl:16])=O.O[CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24](CO)=[CH:23][C:22]=1[F:30].Cl[C:32]([Cl:35])(Cl)Cl>C1C=CC=CC=1>[Cl:16][CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([CH2:32][Cl:35])=[CH:23][C:22]=1[F:30]

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 226301921,4-Benzenedimethanol, 2,5-difluoro-

Product 1

HCID 21332303alpha,alpha'-Dichloro-2,5-difluoro-para-xylene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

While cooling with ice, 3 g of triethylamine are added to a mixture of 25 g of phosphorus pentachloride and 25 g of phosphorus oxychloride. After that, a solution of 2.2 g of α,α'-dihydroxy-2,5-difluoro-para-xylene in 10 ml of tetrachloromethane are added. The batch is heated at 70° C. for two hours. It is then cooled, poured onto ice, and dissolved in benzene. The benzene solution is washed with aqueous sodium carbonate solution, then dried with calcium chloride. The solvent is evaporated and the residue recrystallized several times from aqueous methanol. There are obtained 1.85 g of fine colorless needles melting at 62.5 - 64.5° C.

Workup

  1. temperatureIt is then cooled
  2. additionpoured onto ice
  3. washThe benzene solution is washed with aqueous sodium carbonate solution
  4. dry with materialdried with calcium chloride
  5. customThe solvent is evaporated
  6. customthe residue recrystallized several times from aqueous methanol

Sources & evidence

ORD record
ord-6a17fcba63804977894d0c2c861704a7
Source dataset
uspto-grants-1979_02
Patent number
US04140843

Reaction notes

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