2,3,4,5,6-Pentafluorobenzyl Alcohol → Pentafluorobenzyl fluoride

HRID 354710

Reaction equation

HRID 354710 reaction equation
[F:1][C:2]1[C:7]([CH2:8]O)=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].ClC(F)C(N(CC)CC)(F)[F:17]>C(Cl)Cl>[F:1][C:2]1[C:7]([CH2:8][F:17])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13]

Participants

4

Reactant 2

HCID 99232,3,4,5,6-Pentafluorobenzyl AlcoholHCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine

Product 1

HCID 12701527Pentafluorobenzyl fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of pentafluorobenzyl alcohol (3.0 g) and dry methylene dichloride (50 ml) was cooled to a temperature of 0° C. in an ice-bath and 2-chloro-1-diethylamino-1,1,2-trifluoroethane (4.3 g) was slowly added to the cooled, stirred mixture over a period of ten minutes. After standing for a period of 18 hr at 0° C. the reaction mixture was poured into ice and the organic layer was separated and washed with IM aqueous sodium carbonate solution. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation and the product was distilled under reduced pressure to give pentafluorobenzyl fluoride, b.p. 51° C. at 30 mm Hg.

Workup

  1. additionthe reaction mixture was poured into ice
  2. customthe organic layer was separated
  3. washwashed with IM aqueous sodium carbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation
  6. distillationthe product was distilled under reduced pressure

Sources & evidence

ORD record
ord-933997dc546f4109b08b91bff02b2dcd
Source dataset
uspto-grants-1983_03
Patent number
US04376784

Linked notes

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