Pyridine → HCID 57148770, compound

HRID 1395213Notes

Reaction equation

HRID 1395213 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])=[C:13]([CH3:16])[CH2:14]O)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.P(Br)(Br)[Br:25]>CCCCC>[C:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])=[C:13]([CH3:16])[CH2:14][Br:25])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 57321997HCID 57321997, compound

Product 1

HCID 57148770HCID 57148770, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A mixture of 72 g of 3-(p-tert.amyl-phenyl)-2,3-dimethyl-allyl alcohol and 7.2 ml of pyridine in 500 ml of n-pentane is cooled down to -5° C. At this temperature there are added dropwise while stirring over a period of 2 hours 40.2 g of phosphorus tribromide in 500 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 crude 3-(p-tert.amyl-phenyl)-2,3-dimethyl-allyl bromide obtained [NMR: 60 Mc, CDCl3 →1-CH2 =3.9 and 4.1 ppm (2s)] was used in the process without further purification.

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

Sources & evidence

ORD record
ord-5bfd68dae7b840ad88280466c161f30f
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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