Hydrogen Bromide → 2-(alpha,alpha,beta,beta-Tetrafluorophenethyl)benzyl bromide

HRID 1834860Notes

Reaction equation

HRID 1834860 reaction equation
[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]O)([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BrH:21]>>[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][Br:21])([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 54078599HCID 54078599, compound

Product 1

HCID 203722852-(alpha,alpha,beta,beta-Tetrafluorophenethyl)benzyl bromide

Procedure

A suspension of 3.3 g. (0.0116 mole) of 2-(α,α,β,β-tetrafluorophenethyl)benzyl alcohol in 15 ml. of 48% hydrobromic acid is stirred and heated on the steam bath for 3 hours. The product crystallizes from the cooled mixture and is collected and dissolved in benzene. Evaporation of the washed and dried benzene extract under reduced pressure and sublimation of the residual solid at 60° C. and 0.05 mm. yields white crystals, m.p. 70°-77° C. A sample for analysis from a previous preparation was purified by column chromatography on silica, eluting the product with benzene-carbon tetrachloride (2:1). The fractions that showed one spot of rf 0.85 on a fluorescent silica, thin layer plate developed with benzene were combined and the solvent evaporated under reduced pressure. The residual solid, m.p. 78°-82° C., was sublimed at 60° C. and 0.05 mm. to yield product, m.p. 80.5°-82° C.

Workup

  1. additionA suspension of 3.3 g
  2. temperatureheated on the steam bath for 3 hours
  3. customThe product crystallizes from the cooled mixture
  4. customis collected
  5. dissolutiondissolved in benzene
  6. customEvaporation of the
  7. washwashed
  8. extractiondried benzene extract under reduced pressure and sublimation of the residual solid at 60° C.
  9. customyields white crystals, m.p. 70°-77° C
  10. customA sample for analysis from a previous preparation
  11. customwas purified by column chromatography on silica
  12. washeluting the product with benzene-carbon tetrachloride (2:1)
  13. customthe solvent evaporated under reduced pressure
  14. customwas sublimed at 60° C.
  15. customto yield product, m.p. 80.5°-82° C.

Sources & evidence

ORD record
ord-db9af0ac51ac40e98cc8989b0cc0829a
Source dataset
uspto-grants-1978_01
Patent number
US04071570

Reaction notes

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