Sodium Iodide → Diphenylacetylene

HRID 1751939Notes

Reaction equation

HRID 1751939 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[I-].[Na+]>>[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 7961BromobenzeneHCID 10821Phenylacetylene

Product 1

HCID 10390DiphenylacetyleneYield 90%

Procedure

Following General Procedure C (120° C., 30 hours), phenylacetylene (84 μL, 1.5 mmol) was coupled with bromobenzene (106 μL, 1.0 mmol), in the presence of sodium iodide (NaI; 0.5 eq.; 0.5 mmol). The crude brown oil was purified by flash chromatography on silica gel to provide 90% 1,1′-ethyne-1,2-diyldibenzene.

Workup

  1. customThe crude brown oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e933bf772a0c4a64b906dea54f569860
Source dataset
uspto-grants-2015_10
Patent number
US09162953B2

Reaction notes

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