Benzene → 3,3,3-Trifluoropropylbenzene

HRID 1603288Notes

Reaction equation

HRID 1603288 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]([CH2:9][CH2:10]F)([F:8])([F:7])[F:6].Cl.[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[F:6][C:5]([F:8])([F:7])[CH2:9][CH2:10][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 27767241,1,1,3-TetrafluoropropaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1933303,3,3-Trifluoropropylbenzene

Procedure

To a slurry of 9.4 g AlCl3 in 90 mL benzene cooled in an ice bath, was added (over 18 minutes) a solution of 14.2 g of CF3CH2CH2F in 10 mL benzene. The mixture was stirred for an additional 0.5 hour at ice-bath temperature and 1 hour at room temperature. It was then poured into 50 g ice and 25 mL concentrated HCl, and the resulting solution stirred until the color disappeared. The benzene layer was separated, washed with 25 mL saturated NaCl and dried (Na2SO4). Distillation provided 1,1,1-trifluoro-3-phenylpropane (CH3CH2CH2Ph), bp 77-79° C. at 32 mm Hg. 1H NMR: 7.1(5H), 2.8(m) ppm. 19F NMR: -67.2 (t, J=9.7 Hz) ppm. This example shows the utility of CF3CH2CH2F. It illustrates that it can be used in a Friedel-Crafts reaction to make the same product as would be obtained if CF3CH=CH2 had been used.

Workup

  1. stirringthe resulting solution stirred until the color
  2. customThe benzene layer was separated
  3. washwashed with 25 mL saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. distillationDistillation

Sources & evidence

ORD record
ord-d7a9f93d02d74eb4a6432a697522e2a3
Source dataset
uspto-grants-1999_11
Patent number
US05986151

Reaction notes

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