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

HRID 1843036Notes

Reaction equation

HRID 1843036 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[F:13].O=S(Cl)Cl.[CH3:18][CH2:19]O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([O:11][CH2:18][CH3:19])=[O:10])=[CH:4][C:3]=1[F:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 130652312-(4-Amino-3-fluorophenyl)propanoic acid

Product 1

HCID 20364696Ethyl 2-(4-amino-3-fluorophenyl)propanoateYield 87%

Procedure

To a solution of 2-(4-Amino-3-fluorophenyl)propionic acid (1 g, 5.459 mmol) in EtOH was added SOCl2 (0.6 ml, 8.189 mmol) at 0° C. The mixture was stirred for 2 hours at room temperature and then SOCl2 was removed under reduced pressure. The residue was diluted with EtOAc and washed with a saturated NaHCO3 solution. The resulting mixture was dried over MgSO4 and concentrated. The residue was purified by column chromatography to afford ethyl 2-(4-amino-3-fluorophenyl)propanoate (1 g, 87%).

Workup

  1. customSOCl2 was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with a saturated NaHCO3 solution
  4. dry with materialThe resulting mixture was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-79ca0700f8bd465ea5f1e26d92067418
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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