Bromine → HCID 19872310, compound

HRID 477753Notes

Reaction equation

HRID 477753 reaction equation
C([Li])CCC.[CH2:6]([S:13][C:14]1[N:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:25]Br>O1CCCC1>[CH2:6]([S:13][C:14]1[N:18]=[C:17]([Br:25])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 772049HCID 772049, compoundHCID 178418339Butyllithium

Product 1

HCID 19872310HCID 19872310, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (50 ml) was added dropwise to a stirred solution of 3-benzylthio-1-phenyl-1,2,4-triazole (31.8 g) in dry tetrahydrofuran (200 ml) at -70° C. Bromine (19 g) was added and the reaction mixture was allowed to warm to room temperature and then quenched with water. After washing with brine, the organic phase was dried and evaporated to give a yellow oil. Purification by chromatography over silica with dichloromethane and petroleum ether afforded the desired product as a pale yellow oil.

Workup

  1. customquenched with water
  2. washAfter washing with brine
  3. customthe organic phase was dried
  4. customevaporated
  5. customto give a yellow oil
  6. customPurification by chromatography over silica with dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-712ce6e789264c7ba86f7bd136e75042
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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