1,2-Dibromoethane → HCID 13650453, compound

HRID 2290751Notes

Reaction equation

HRID 2290751 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.[CH2:16]1OCCOCCOCCOCCOCCO[CH2:17]1.[OH-].[K+].BrCCBr>C(Cl)Cl>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH2:17][CH2:16]2)=[O:8])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 104204761-(4-Fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Product 1

HCID 13650453HCID 13650453, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1H-1,2,4-triazol-1-yl)-4'-fluoroacetophenone (10.24 g, 50 mMole) in methylene chloride (70 ml) was added 18-Crown-6 ether (1 g) (trade mark for 1,4,7,10,13,16-hexaoxacyclooctadecane) and potassium hydroxide (6.1 g, 109 mMole) with stirring. Ten minutes later 1,2-dibromoethane was added (10.3 g, 55 mMole in one batch. Stirring was continued for 18 hours. The mixture was poured into saturated saline solution (100 ml) and the organic phase was separated, washed with water (3×30 ml) and dried over anhydrous magnesium sulphate. Evaporation gave an oil, weight 13.7 g. Purification was carried out by flash column chromatography under slight pressure (2 p.s.i.) on a Merck "Kieselgel 60" (trade mark) 230-400 mesh fractions after collection and evaporation gave a solid, the pure title compound, 2.9 g, m.p. 73°-75° (25% yield).

Workup

  1. stirringStirring
  2. customthe organic phase was separated
  3. washwashed with water (3×30 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation
  6. customgave an oil, weight 13.7 g
  7. customPurification
  8. customafter collection and evaporation
  9. customgave a solid

Sources & evidence

ORD record
ord-08f38186bbaf4be58f8aa29e8a73f655
Source dataset
uspto-grants-1986_10
Patent number
US04618616

Reaction notes

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