1-Ethynyl-4-propylbenzene → Diphenylacetylene

HRID 1707212Notes

Reaction equation

HRID 1707212 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](C#C)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH2:12](SC1C=CC(I)=CC=1)[CH2:13][CH2:14][CH2:15][CH3:16]>C(NCC)C.[Cu]I>[C:4]1([C:1]#[C:2][C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 27751331-Ethynyl-4-propylbenzeneHCID 189826561-Iodo-4-(pentylthio)benzene

Product 1

HCID 10390DiphenylacetyleneYield 123.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
20 °C

Procedure

The product from step 2.4 (2.82 g) and the product from step 2.2 (6.0 g) were mixed in diethylamine (44 ml). Copper (I) iodide (0.026 g) and dichloro di(triphenylphosphine) palladium (0) (0.193 g) were then added and the mixture was then stirred at 20° C. under argon for 16 hrs. Purification by chromatography gave 4.3 g of tolane product, mpt. 43° C.

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-5a030c97fd674e7d94b450d6c638b3e6
Source dataset
uspto-grants-1994_10
Patent number
US05352381

Reaction notes

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