1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene → HCID 67218075, compound

HRID 1505235Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N+:11]=[N-:12])=[CH:6][C:5]=1[CH3:13].[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23])[CH:19]=[C:18]([Cl:28])[CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:23][C:22]([C:20]3[CH:19]=[C:18]([Cl:28])[CH:17]=[C:16]([Cl:15])[CH:21]=3)([C:24]([F:25])([F:27])[F:26])[N:12]=[N:11]2)=[CH:6][C:5]=1[CH3:13]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-azido-2-methyl-benzoic acid methyl ester (made in analogy to methods described in, for example, Journal of Organic Chemistry, 2006, 71(15), 5822-5825) (820 mg, 3.4 mmol) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (preparation described in, for example, EP 1,731,512) (500 mg, 2.6 mmol) in toluene (20 ml) was heated at 130° C. for 48 hours. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel (eluent: 3% v/v ethyl acetate in hexane) to give 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-[1,2,3]triazol-1-yl]-2-methyl-benzoic acid methyl ester as a gummy oil (200 mg).

Workup

concentrationThe reaction mixture was concentrated
customthe residue purified by column chromatography on silica gel (eluent: 3% v/v ethyl acetate in hexane)

Sources & evidence

ORD record: ord-e10a49f45c0e49e49a95fa48ab0286c0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216973B2

Reaction notes

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