Pyridine → 3-(p-Tert.butyl-phenyl)-2-methyl-allyl bromide

HRID 1733274Notes

Reaction equation

HRID 1733274 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:15])[CH2:13]O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.P(Br)(Br)[Br:23]>CCCCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:15])[CH2:13][Br:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 543813673-(4-tert-Butylphenyl)-2-methylprop-2-en-1-ol

Product 1

HCID 572041753-(p-Tert.butyl-phenyl)-2-methyl-allyl bromide

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

73.2 g of 3-(p-tert.butyl-phenyl)-2-methyl-allyl alcohol nd 8.6 ml of pyridine in 700 ml of n-pentane are cooled down to -5° C. At this temperature there are added dropwise while stirring over a period of 2 hours 15.2 ml of phosphorus tribromide in 700 ml of n-pentane and the mixture is stirred at room temperature for 3 hours. The mixture is poured on to 500 g of ice and stirred up for 30 minutes. The pentane phase is separated and the aqueous phase is back-extracted with n-pentane. The combined n-pentane phases are washed neutral with saturated sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The 3-(p-tert.butyl-phenyl)-2-methyl-allyl bromide, distilled in a high vacuum, boils at 123° C./0.01 Torr.

Workup

  1. additionAt this temperature there are added dropwise
  2. stirringstirred up for 30 minutes
  3. customThe pentane phase is separated
  4. extractionthe aqueous phase is back-extracted with n-pentane
  5. washThe combined n-pentane phases are washed neutral with saturated sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. distillationThe 3-(p-tert.butyl-phenyl)-2-methyl-allyl bromide, distilled in a high vacuum, boils at 123° C./0.01 Torr

Sources & evidence

ORD record
ord-c790d7e2e6e84c52b4a53e8f8046ec12
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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