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

HRID 1462149Notes

Reaction equation

HRID 1462149 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 mixture 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 afterwards 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.

Workup

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

Sources & evidence

ORD record
ord-4a6f42d47b9e402dbba02331dddd4d95
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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