Dimethyl Sulfoxide → 4-Ethynyl-1,1'-biphenyl

HRID 918030

Reaction equation

HRID 918030 reaction equation
CC(C)([O-])C.[K+].CS(C)=O.Br[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:13]Br>C(O)(C)(C)C>[CH:13]#[C:12][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 12788040HCID 12788040, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 344644-Ethynyl-1,1'-biphenylYield 90.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 26 g of potassium t-butoxide in 400 ml of a 1:1 mixture (v/v) of dimethyl sulfoxide and t-butanol at 10°-15° was added with stirring a solution of 39 g of 4-(1,2-dibromoethyl)biphenyl in 400 ml of the same solvent mixture. After stirring for 20 minutes, the reaction mixture was poured into ice-water. The resulting mixture was extracted with diethyl ether. The diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water, and dried over anhydrous sodium sulfate. The diethyl ether was distilled under reduced pressure and the solid residue crystallized from aqueous ethanol to give 18.5 g of crude 4-biphenylacetylene, mp 79°-81°. Two recrystallizations from hexane gave pure 4-biphenylacetylene, mp 82°-85°. The following elemental analysis was obtained:

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. washThe diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe diethyl ether was distilled under reduced pressure
  5. customthe solid residue crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-0206847ad9194784bb54ffcb6065814f
Source dataset
uspto-grants-1976_07
Patent number
US03968251

Linked notes

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