Ethyl 4,4,4-trifluoro-2-butynoate → 3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazole-4-carboxylic Acid Ethyl Ester

HRID 424810Notes

Reaction equation

[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].[CH2:12]([O:14][C:15](=[O:22])[C:16]#[C:17][C:18]([F:21])([F:20])[F:19])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15]([C:16]1[N:1]([C:4]2[C:5]([Cl:11])=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:10])[N:2]=[N:3][C:17]=1[C:18]([F:19])([F:20])[F:21])=[O:22])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-Azido-1,3-dichloro-benzene (25.0 g, 132.9 mmol) and 4,4,4-trifluoro-but-2-ynoic acid ethyl ester (26.5 g, 159.6 mmol) in toluene (30 mL) are heated at 80° C. for 18 h. A large exotherm is observed at 25 minutes. The reaction is removed from heat until exotherm subsides. Two regioisomers are observed in a range of 1:1 to 3:1 in favor of the desired product. The reaction mixture is concentrated under reduced pressure to 51 g of crude material and purified via column chromatography using a gradient of 35-60% DCM in Hexanes to yield the title compound (28 g, 59%). ES/MS m/e 353.0 (M+1).

Workup

customThe reaction is removed
temperaturefrom heat until exotherm subsides
concentrationThe reaction mixture is concentrated under reduced pressure to 51 g of crude material
custompurified via column chromatography

Sources & evidence

ORD record: ord-2c1b7ce6f18742798249fd534c821472
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

Loading…