Hydrogen Bromide → HCID 13533275, compound

HRID 846623Notes

Reaction equation

HRID 846623 reaction equation
O1CCOCC1.[CH:7]1([CH:10](O)[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH2:9][CH2:8]1.[BrH:20]>O>[CH3:18][S:17][C:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[CH:7]/[CH2:8][CH2:9][Br:20])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 312751,4-DioxaneHCID 14988329α-Cyclopropyl-4-(methylthio)benzenemethanol

Product 1

HCID 13533275HCID 13533275, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of dioxane solution containing 5 g of 1-(cyclopropyl, hydroxymethyl)-4-methylthiobenzene was added dropwise 6 ml of 47% of hydrobromic acid under an ice-cooled condition, then the mixture was stirred for 30 minutes, and the reaction mixture was concentrated under a reduced pressure. To the residue thus obtained was added water, then extracted with ether, the extract was washed with water and dried with anhydrous sodium sulfate, and concentrated to dryness. The residue was recrystallized from methanol to yield 2.2 g of 4-(4'-methylthiophenyl)-3(E)-butenylbromide in the form of colorless flake-like crystals. Melting point: 54°-56° C.

Workup

  1. temperaturecooled condition
  2. concentrationthe reaction mixture was concentrated under a reduced pressure
  3. customTo the residue thus obtained
  4. extractionextracted with ether
  5. washthe extract was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-18a6d7783d57477596a93920632ae195
Source dataset
uspto-grants-1992_08
Patent number
US05137889

Reaction notes

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