Phenethyl bromide → HCID 19068911, compound

Temperature

60 °C

118 g of tert-butyl dimethylphosphonoacetate were dissolved, under a nitrogen atmosphere, in 875 ml of dry dimethylformamide. 58.9 g of potassium tert-butoxide were added to the solution while cooling with ice. The reaction mixture was subsequently heated at 60° C. for a short period and then allowed to cool down 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 the working-up, most of the dimethylformamide was evaporated under reduced pressure and the remaining residue was dissolved in methyl tert-butyl ether. The solution was acidified with aqueous potassium hydrogen sulfate 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 the eluent. 105.1 g of pure tert-butyl 2-(dimethylphosphono)-4-phenyl-n-butyrate were obtained as an oily product.

1. temperaturewhile cooling with ice
2. temperatureto cool down to room temperature
3. temperatureThe reaction mixture was then heated at 60° C. for 2 hours
4. customwas evaporated 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

ORD record

ord-e54536ea9c5442a69197058d320a0bbf

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05783573