4-(Trifluoromethyl)benzoyl chloride → 3-(3-Bromo-thiophen-2-yl)-5-(4-trifluoromethyl-phenyl)-[1,2,4]-oxadiazole

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[Br:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20](=[N:22]O)[NH2:21]>>[Br:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]1[N:22]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)[O:8][N:21]=1

Participants

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chloride

HCID 865873543-Bromo-thiophene-2-amidoxime

Product 1

HCID 221479173-(3-Bromo-thiophen-2-yl)-5-(4-trifluoromethyl-phenyl)-[1,2,4]-oxadiazole

Procedure

The title compound was prepared from 4-trifluoromethyl-benzoyl chloride (66 μL, 0.44 mmol) and 3-bromo-thiophene-2-amidoxime (98 mg, 0.44 mmol) similar to Example 16, and yielded 130 mg (78%) of white solid.

Sources & evidence

ORD record: ord-802e7b6698ef4cbfbd5d2e7dc0604c31
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435750B2

Reaction notes

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