Water → 1-Ethyl-4-ethynylbenzene

HRID 2398495

Reaction equation

HRID 2398495 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][CH:5]=1.O1CCCC1.C([Li])CCC.O>CCCCCC>[CH2:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]#[CH:2])=[CH:5][CH:6]=1)[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 214353101,1-Dibromo-2-(4-ethylphenyl)ethyleneHCID 178418339Butyllithium

Product 1

HCID 1424251-Ethyl-4-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1,1-Dibromo-2-(4-ethylphenyl)ethylene (1.1 g., 3.69 mmol.) is dissolved in 20 ml. of dry tetrahydrofuran and maintained under a nitrogen atmosphere. The solution is cooled to -78° and 3.9 ml. of a 1.9 M solution of butyl lithium in hexane is added with stirring. The reaction mixture is stirred one hour at -78°, then warmed to ambient temperature and stirred an additional hour. Water is added, the mixture is extracted with petroleum ether, the extracts are combined, dried (MgSO4) and concentrated to give 4-ethylphenylacetylene.

Workup

  1. temperatureThe solution is cooled to -78°
  2. stirringThe reaction mixture is stirred one hour at -78°
  3. stirringstirred an additional hour
  4. extractionthe mixture is extracted with petroleum ether
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05d6ea590dd54c67b6668c445eaf2a11
Source dataset
uspto-grants-1977_05
Patent number
US04024273

Linked notes

Loading…