Phenethyl bromide → HCID 19068911, compound

HRID 1488952Notes

Reaction equation

HRID 1488952 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([O:5][CH3:6])=[O:4].CC(C)([O-])C.[K+].[CH2:21](Br)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH3:1][O:2][P:3]([CH:7]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19068911HCID 19068911, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

118 g of tert-butyl dimethylphosphonoacetate were dissolved in 875 ml of dried dimethylformamide under a nitrogen atmosphere. 58.9 g of potassium tert-butoxide were added to the solution while cooling in ice. The reaction mixture was subsequently heated to 60° C. for a short time and then allowed to cool to room temperature. A solution of 104.9 g of phenethyl bromide in 110 ml of dimethylformamide was added dropwise to the reaction mixture. The reaction mixture was then heated at 60° C. for 2 hours. For working up, the dimethylformamide was substantially evaporated off under reduced pressure, and the remaining residue was dissolved in methyl tert-butyl ether. The solution was acidified with aqueous potassium bisulfate solution. The organic phase was then separated, washed with water, dried over sodium sulfate and evaporated under reduced pressure. The resulting crude product was purified by flash chromatography on 3 kg of silica gel using dichloromethane/methyl tert-butyl ether (4:1) as eluent. 105.1 g of pure tert-butyl 2-(dimethylphosphono)-4-phenyl-n-butyrate were obtained as an oily product.

Workup

  1. temperaturewhile cooling in ice
  2. temperatureto cool to room temperature
  3. temperatureThe reaction mixture was then heated at 60° C. for 2 hours
  4. customthe dimethylformamide was substantially evaporated off under reduced pressure
  5. dissolutionthe remaining residue was dissolved in methyl tert-butyl ether
  6. customThe organic phase was then separated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated under reduced pressure
  10. customThe resulting crude product was purified by flash chromatography on 3 kg of silica gel

Sources & evidence

ORD record
ord-d876260b58494d8684ba516ecbd405e6
Source dataset
uspto-grants-1997_10
Patent number
US05677297

Reaction notes

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