Boron trifluoride → 1-tert-Butyl-4-(3-chloro-2-methylpropyl)benzene

HRID 1413419Notes

Reaction equation

HRID 1413419 reaction equation
B(F)(F)F.[CH3:5][CH:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][Cl:8].B(F)(F)F.O.O.[C:22](Cl)([CH3:25])([CH3:24])[CH3:23]>O>[CH3:5][CH:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][Cl:8].[CH3:5][CH:6]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:12][CH:11]=1)[CH2:7][Cl:8]

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 10486tert-BUTYL CHLORIDEHCID 61591Boron trifluoride dihydrateHCID 13510156(3-Chloro-2-methylpropyl)benzene

Product 2

HCID 132518171-tert-Butyl-4-(3-chloro-2-methylpropyl)benzeneHCID 13510156(3-Chloro-2-methylpropyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

BF3 is passed for 30 minutes into a mixture of 84 parts by weight of 2-methyl-3-phenyl-propyl chloride and 50 ml of BF3.2H2O at room temperature. 56 parts by weight of tert.-butyl chloride are then added dropwise at room temperature. The mixture is refluxed for 4 hours and is then allowed to cool; the crude product is introduced into water and extracted with chloroform. The organic phase is separated off, washed with water, dried over Na2CO3 and distilled. 30 parts by weight of 2-methyl-3-phenyl-propyl chloride, boiling point 105° C./16 mm Hg, and 45 parts by weight of 2-methyl-3-(p-tert.-butylphenyl)-propyl chloride, boiling point 80°-81° C./0.02 mm Hg, are obtained.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. temperatureto cool
  3. extractionextracted with chloroform
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materialdried over Na2CO3
  7. distillationdistilled

Sources & evidence

ORD record
ord-013c55b177b14307871aeacf95c9398c
Source dataset
uspto-grants-1981_02
Patent number
US04250123

Reaction notes

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