Water → 1-(3-Bromo-2-methyl-1-propenyl)-4-isopropylbenzene

HRID 272345Notes

Reaction equation

HRID 272345 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([CH3:14])[CH2:12]O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].P(Br)(Br)[Br:16].O>C(OC(C)C)(C)C>[Br:16][CH2:12][C:11]([CH3:14])=[CH:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 68704626HCID 68704626, compound

Product 1

HCID 687079861-(3-Bromo-2-methyl-1-propenyl)-4-isopropylbenzeneYield 136.4%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 3-(4-isopropylphenyl)-2-methyl-2-propen-1-ol (6.30 g, 33.1 mmol) in isopropyl ether (50 ml) was added under ice cooling phosphorus tribromide (5.98 g, 22.1 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction mixture and the product was extracted with isopropyl ether. The organic layer was washed with water and an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain 7.63 g (91% yield) of the oily title compound.

Workup

  1. extractionthe product was extracted with isopropyl ether
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12c08149c6c647e090bad6538b85819d
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

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