2-Fluoroethyl bromide → HCID 22903561, compound

HRID 1488941Notes

Reaction equation

HRID 1488941 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:10][NH2:11])=[O:9])=[CH:6][CH:5]=1.Br[CH2:15][CH2:16]F>O.C(O)C>[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]2[O:9][CH:15]=[CH:16][NH:11][N:10]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 14798Sodium HydroxideHCID 222194-Bromobenzohydrazide

Product 1

HCID 22903561HCID 22903561, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2.9 g (0.07 mole) sodium hydroxide dissolved in 10 ml of water was added dropwise at room temperature to a mixture of 6.5 g (0.03 mole) 4-bromobenzoic hydrazide and 4.0 g (0.03 mole) 1-bromo-2-fluoroethane in 25 ml of ethanol. The resulting solution was refluxed for two and one-half hours. The mixture was cooled to room temperature, diluted with 150 ml of water and extracted several times with ether (100 ml). After separation and drying over anhydrous sodium sulfate, the solution was filtered and evaporated under reduced pressure leaving 4.6 grams of an oil (63.6% yield), which was purified by distillation. The product was characterized by IR and NMR spectroscopy.

Workup

  1. temperatureThe resulting solution was refluxed for two and one-half hours
  2. extractionextracted several times with ether (100 ml)
  3. customAfter separation
  4. dry with materialdrying over anhydrous sodium sulfate
  5. filtrationthe solution was filtered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e29e9a310db840209e794ed1eb86cae5
Source dataset
uspto-grants-1997_10
Patent number
US05677301

Reaction notes

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