Bromine → HCID 21185375, compound

HRID 1385641Notes

Reaction equation

HRID 1385641 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-4dfc420a38cf4177adf79108762e816a
Source dataset
uspto-grants-2001_07
Patent number
US06262305B1

Reaction notes

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