Bromine → HCID 21185375, compound

HRID 850039Notes

Reaction equation

HRID 850039 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[S:20][C:21](Cl)=[C:22]([Cl:25])[C:23]=2[Cl:24])[N:16]([CH3:27])[N:15]=1.[Br:28]Br>C1COCC1.O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[S:20][C:21]([Br:28])=[C:22]([Cl:25])[C:23]=2[Cl:24])[N:16]([CH3:27])[N:15]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 21185385HCID 21185385, compoundHCID 178418339Butyllithium

Product 1

HCID 21185375HCID 21185375, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.5 mmol) was slowly added to a solution of 3-(2,6-dichlorophenyl)-5-(3,4,5-trichlorothien-2-yl)-1-methyl[1,2,4]triazole (325 mg, 1.0 mmol) in THF at -78° C., and the mixture was stirred one hour. Bromine (3.0 mmol) was added and the reaction stirred two hours, then diluted with water, extracted with ether, washed with brine, and dried over magnesium sulfate. The product was concentrated to 620 mg of dark oil. This was chromatographed (SiO2, 10% EtOAc-Hex) to give 79 mg of the title product as a pink solid. MP 197-199° C.

Workup

  1. stirringthe reaction stirred two hours
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe product was concentrated to 620 mg of dark oil
  6. customThis was chromatographed (SiO2, 10% EtOAc-Hex)

Sources & evidence

ORD record
ord-faa2b29b96d440a7ac1e21a7e33e167a
Source dataset
uspto-grants-2000_01
Patent number
US06015826

Reaction notes

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