Ethanol → Ethyl 2-amino-3-(4-bromophenyl)propanoate

HRID 509082Notes

Reaction equation

HRID 509082 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].O=S(Cl)Cl.[CH3:18][CH2:19]O>>[CH2:18]([O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 856814-Bromophenylalanine

Product 1

HCID 4016808Ethyl 2-amino-3-(4-bromophenyl)propanoateYield 72%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-3-(4-bromophenyl)propanoic acid (40 g, 164 mmol) in EtOH (100 mL) was added SOCl2 (30 ml, 422 mmol) dropwise at 80° C. The mixture was stirred at 80° C. for 2 hrs. After the solvent was evaporated, the residue was extracted by EA. The combined organic layers were washed with aqueous NaCl, dried by anhydrous Na2SO4, and concentrated in vacuo to afford ethyl-2-amino-3-(4-bromophenyl)propanoate as a yellow liquid (32 g, yield: 72%).

Workup

  1. customAfter the solvent was evaporated
  2. extractionthe residue was extracted by EA
  3. washThe combined organic layers were washed with aqueous NaCl
  4. dry with materialdried by anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12f89228bd34420f966beb076effc6c4
Source dataset
uspto-grants-2015_08
Patent number
US09096549B2

Reaction notes

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