N-bromobutanimide → 1-(2-Fluoro-4-chloro-5-bromophenyl)-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one

HRID 636837Notes

Reaction equation

HRID 636837 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:16])[F:15])[C:10]([CH3:17])=[N:9]2)=[C:4]([F:18])[CH:3]=1.[Br:19]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([Br:19])=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:15])[F:16])[C:10]([CH3:17])=[N:9]2)=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 9882096Chloro Fluoro Triazolin-3-one

Product 1

HCID 212559541-(2-Fluoro-4-chloro-5-bromophenyl)-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-oneYield 62.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

This compound was prepared in the manner of Example 1 with 7.6 grams (0.027 mole—1.0 equiv.) of 1-(4-chloro-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, 10.0 grams (0.056 mole—2.1 equiv.) of N-bromosuccinimide, and 50 mL of concentrated sulfuric acid (% wt/vol. triazole to solvent—15.2%) as reagents. A yield of 6.06 grams of 92.4% pure 1-(4-chloro-2-fluoro-5-bromophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole (62.1% yield) was obtained.

Sources & evidence

ORD record
ord-79f7bf692ef34059aea92a17b2aeb577
Source dataset
uspto-grants-2001_02
Patent number
US06194583B1

Reaction notes

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