Bromotrichloromethane → (Bromoethynyl)benzene

HRID 654608Notes

Reaction equation

HRID 654608 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9]C(Cl)(Cl)Cl>O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C#C)C=CC=CC=1>[Br:9][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6383BromotrichloromethaneHCID 10821Phenylacetylene

Product 1

HCID 136737(Bromoethynyl)benzeneYield 95%

Reagents, catalysts & solvents 2

HCID 10821PhenylacetyleneCatalystHCID 11726816Tetrabutylammonium Fluoride TrihydrateCatalyst

Procedure

In a 10 mL round-bottom flask, 1.02 g of phenylacetylene (10 mmol), 2.1 g bromotrichloromethane (10.5 mmol) and 100 mg of tetra-n-butylammonium fluoride trihydrate (0.316 mmol) were stirred at 24° C. for 15 min. The temperature of the mixture rose to 33° C. in the course of the process. Analysis of the resulting mixture showed that it contained 1.72 g of 1-bromo-2-phenylacetylene (95% yield) and 0.05 g of the unconverted phenylacetylene.

Workup

  1. customrose to 33° C. in the course of the process

Sources & evidence

ORD record
ord-0484acd9f3944462977eedecda75db40
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Reaction notes

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