Trimethylsilylacetylene → 1-(2-Bromo-5-fluorophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole

HRID 1726663Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[Br:11])=[N+:2]=[N-:3].[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[Br:11][C:5]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=1[N:1]1[CH:17]=[C:16]([Si:13]([CH3:15])([CH3:14])[CH3:12])[N:3]=[N:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-azido-1-bromo-4-fluorobenzene (1.047 g, 4.85 mmol) and trimethylsilylacetylene (2.01 mL, 14.54 mmol) in toluene (5 mL) was heated in a pressure vessel at 110° C. for 21.5 h. The reaction mixture was concentrated in vacuo and the residue was purified with a Biotage system on silica gel with hexanes:ethyl acetate (9:1) gradient as the eluent to afford the title compound as a colorless oil (1.451 g, 95% yield): 1H NMR (400 MHz, CDCl3) δ ppm: 7.97 (1H, s), 7.74 (1H, dd, J=9.0, 5.4 Hz), 7.37 (1H, dd, J=8.5, 2.9 Hz), 7.16 (1H, ddd, J=8.8, 7.6, 3.0 Hz), 0.40 (9H, s), LCMS (+ESI, M+H+) m/z 314/316.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified with a Biotage system on silica gel with hexanes:ethyl acetate (9:1) gradient as the eluent

Sources & evidence

ORD record: ord-9dc914eba7dd46a7a16ff1da205392de
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491819B1

Reaction notes

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