Benzonitrile → Diphenylacetylene

HRID 2213956Notes

Reaction equation

HRID 2213956 reaction equation
[C:1]1([C:7]#[C:8][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCCCCCCCCCCCC>C1COCC1.[Zn+2].[Br-].[Br-]>[C:1]1([C:7]#[C:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7505Benzonitrile2×HCID 12388TridecaneHCID 178419644HCID 178419644, compound

Product 1

HCID 10390DiphenylacetyleneYield 31.5%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of phenylethynylmagnesium bromide (4.0 ml; 4.00 mmol; 1.0 M in THF) in was treated at room temperature with a solution of ZnBr2 (0.473 g; 2.10 mmol) in THF (1 ml) and stirred for 30 min. This solution was then added to a room temperature solution of benzonitrile (0.204 ml; 0.206 g; 2.00 mmol), dichlorobis(trimethylphosphine)nickel (0.0282 g; 5 mol %), and tridecane (0.244 ml; 0.184 g; 1.00 mmol) in THF (1 ml). The reaction mixture was then heated to 65° C. and stirred for 46 h; then a sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and MTBE. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 0.63 mmol (31% yield) of diphenylacetylene and 0.36 mmol of benzonitrile remaining in the reaction mixture.

Workup

  1. stirringstirred for 46 h
  2. customthen a sample was withdrawn
  3. customquenched in a mixture of 1 M sodium citrate (aq) and MTBE

Sources & evidence

ORD record
ord-a8ef77e36a9d42fdacae3289ac404536
Source dataset
uspto-grants-2006_09
Patent number
US07105707B2

Reaction notes

Loading…