Phenol → 4-(3-Trifluoromethylphenyl)-5-phenoxy-1,2,4-triazole

HRID 64768Notes

Reaction equation

HRID 64768 reaction equation
CC(C)([O-])C.[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O-]CCCC.[F:19][C:20]([F:34])([F:33])[C:21]1[CH:22]=[C:23]([N:27]2[C:31](Cl)=[N:30][N:29]=[CH:28]2)[CH:24]=[CH:25][CH:26]=1>CN(C)C=O>[F:33][C:20]([F:19])([F:34])[C:21]1[CH:22]=[C:23]([N:27]2[C:28]([O:13][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:29][N:30]=[CH:31]2)[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 12476378Butan-1-olateHCID 202353684-(3-Trifluoromethylphenyl)-5-chloro-1,2,4-triazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 202353654-(3-Trifluoromethylphenyl)-5-phenoxy-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

0.8 g of potassium tert-butoxide was added to a solution of 0.53 g of phenol in 10 ml of dry dimethyl formamide. When all the butoxide had dissolved, a solution of 1.4 g of 25B in 10 ml of dry dimethylformamide (10 ml) was added and the stirred mixture was heated to 75° C. for 90 minutes. The reaction mixture was poured into a large excess of ice-water, the solid product filtered off and recrystallized from hexane/ethyl acetate to give 25, as a solid, m.p.: 83°-85° C.

Workup

  1. filtrationthe solid product filtered off
  2. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-2a30eaaded3e44e39ae003b572fa8719
Source dataset
uspto-grants-1986_09
Patent number
US04610717

Reaction notes

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