Phenylacetylene → 1,5-Diphenyl-1,2,3-triazole

HRID 2234227Notes

Reaction equation

CC[Mg+].[Br-].[C:5]1([C:11]#[CH:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:13]1([N:19]=[N+:20]=[N-:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:13]1([N:19]2[C:11]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:12][N:21]=[N:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of EtMgBr in THF (1.0M, 11.9 mL) was added phenylacetylene (1.30 mL, 11.9 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 min. After cooling the mixture to room temperature, a solution of phenylazide (1.41 g, 11.9 mmol) in THF (4 mL) was added. The resulting solution was stirred at room temperature for 30 min, and then heated to 50° C. for 1 hour before quenching with saturated NH4Cl (10 mL). The layers was separated, and the aqueous layer was extracted with CH2Cl2 (10 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the 1,5-diphenyltriazole as a white solid (1.98 g, 75%). 1H NMR (CDCl3, 300 MHz) δ 7.86 (s, 1H), 7.44-7.30 (m, 8H), 7.23-7.20 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 137.6, 136.5, 133.4, 129.3, 129.2, 128.8, 128.5, 126.7, 125.1.

Workup

temperatureAfter cooling the mixture to room temperature
temperatureheated to 50° C. for 1 hour
custombefore quenching with saturated NH4Cl (10 mL)
customThe layers was separated
extractionthe aqueous layer was extracted with CH2Cl2 (10 mL×3)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-ca1436545da342e299a4837af316359f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709655B2

Reaction notes

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