3-(2-Fluorophenyl)prop-2-enoic acid → 3-(2-Fluorophenyl)propanoic acid

HRID 1363672Notes

Reaction equation

HRID 1363672 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([OH:12])=[O:11]>C1COCC1.[Rh]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 679773-(2-Fluorophenyl)prop-2-enoic acid

Product 1

HCID 20638663-(2-Fluorophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-fluoro-phenyl)-acrylic acid (10.00 g, 60.30 mmol) in THF was mixed with Rh/Al2O3 (500 mg) and hydrogenated for 14 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to give 3-(2-fluoro-phenyl)-propionic acid. 3-(2-chloro-phenyl)-propionic acid (10.0 g, 43.70 mmol) was then reacted with SOCl2 (6.60 mL, 90.48 mmol) and AlCl3 (9.00 g, 67.50 mmol) according to the protocols as outlined in general procedure C to afford the title compound. vi Musso, David L.; Cochran, Felicia R.; Kelley, James L.; McLean, Ed W.; Selph, Jeffrey L.; Rigdon, Greg C.; Orr, G. Faye; Davis, Ronda G.; Cooper, Barrett R.; Styles, Virgil L.; Thompson, James B.; Hall, William R. J. Med. Chem. 2003, 46, 399-408.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-21a280669cda441ba5bbbaa02cc4826b
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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