Hexafluorobenzene → 1,2,3,4,5-Pentafluoro-6-(1-methylpropyl)benzene

HRID 2413094Notes

Reaction equation

HRID 2413094 reaction equation
[CH:1]([Li])([CH2:3][CH3:4])[CH3:2].[F:6][C:7]1[C:12](F)=[C:11]([F:14])[C:10]([F:15])=[C:9]([F:16])[C:8]=1[F:17].C(=O)=O.CC(C)=O>C1CCCCC1>[CH:1]([C:12]1[C:11]([F:14])=[C:10]([F:15])[C:9]([F:16])=[C:8]([F:17])[C:7]=1[F:6])([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 9805HexafluorobenzeneHCID 18522661Acetone cardiceHCID 178418400CID 53628100

Product 1

HCID 131276591,2,3,4,5-Pentafluoro-6-(1-methylpropyl)benzene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of sec-butyl lithium (350 ml; 12% in cyclohexane) was added over a period of 1 hour to a stirred mixture of hexafluorobenzene (80 g) in cyclohexane (750 ml) at a temperature of 0° C. On warming the reaction above 0° C. a violently exothermic reaction took place which was brought under control by external cooling (Cardice-acetone). The reaction mixture was subsequently brought to room temperature (no further reaction occurred) and was quenched with water (600 ml). The organic layer was separated, washed with dilute hydrochloric acid (2N; 2×200 ml) and water (2×200 ml) and dried over anhydrous magnesium sulphate and distilled through a 15 cm vigreux column. The fraction distilling at 160°-170° C. was collected to give sec-butylpentafluorobenzene (50.3 g), b.p. 162°-164° C. (760 mm), in the form of a colourless liquid. Hexafluorobenzene is a known compound and is readily available.

Workup

  1. temperatureOn warming
  2. customthe reaction above 0° C.
  3. customa violently exothermic reaction
  4. customwas subsequently brought to room temperature
  5. customno further reaction
  6. customwas quenched with water (600 ml)
  7. customThe organic layer was separated
  8. washwashed with dilute hydrochloric acid (2N; 2×200 ml) and water (2×200 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. distillationdistilled through a 15 cm vigreux column
  11. distillationThe fraction distilling at 160°-170° C.
  12. customwas collected

Sources & evidence

ORD record
ord-adc2db16496b49ae9230c840287480bf
Source dataset
uspto-grants-1985_01
Patent number
US04496390

Reaction notes

Loading…