Hydrogen Bromide → 2-Bromo-3-phenylpropanoic acid
Reaction equation
N[CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BrH:13].N([O-])=O.[Na+]>O>[Br:13][CH:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
15.0 g (165 mmol) of DL-phenylalanine and 37.8 g (317 mmol) were dissolved in 80 ml of water. 25 ml of conc. HBr in water were added at room temperature, and the reaction solution was then cooled to −10° C. While stirring at −10° C., 7.77 g (112 mmol) of sodium nitrite were added in portions over a period of 1 h, and the reaction solution was then stirred at 0° C. for 6 h. The reaction solution was extracted with diethyl ether (4×60 ml), the combined organic phases were dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 18.0 g (86%) of yellow oil
Workup
- stirringthe reaction solution was then stirred at 0° C. for 6 h
- extractionThe reaction solution was extracted with diethyl ether (4×60 ml)
- dry with materialthe combined organic phases were dried over magnesium sulfate
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-7df33b3d28fb48c2849bee69a0407d28
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791148B2
Reaction notes
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