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

HRID 2376303Notes

Reaction equation

HRID 2376303 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 91%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 3-(4-isopropylphenyl)-2-methyl-2-propen-1-ol synthesized in Reference Example 103 (6.30 g, 33.1 mmol) in isopropyl ether (50 mL) was added phosphorus tribromide (5.98 g, 22.1 mmol) with ice-cooling and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution and the mixture was extracted with isopropyl ether. The organic layer was washed with water and a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain the oily title compound 7.63 g (yield 91%)

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with isopropyl ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium hydrogen carbonate solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b30f46b196774932bc792b79b07ebf33
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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