3-(4-Bromo-2,5-difluorophenyl)acrylic acid → 3-(4-Bromo-2,5-difluorophenyl)propanoic acid

HRID 533941Notes

Reaction equation

HRID 533941 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[C:4]([F:14])[CH:3]=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 1

HCID 867151273-(4-Bromo-2,5-difluorophenyl)acrylic acid

Product 1

HCID 848075163-(4-Bromo-2,5-difluorophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-bromo-2,5-difluorophenyl)acrylic acid (4.20 g) in THF was added chlorotris-(triphenylphosphine)rhodium (400 mg). The mixture was stirred at room temperature under H2-atmosphere for 48 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography eluting with DCM/petroleum ether (7:1) to give the subtitle compound as a white solid. MS ESI+: m/z=265 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with DCM/petroleum ether (7:1)

Sources & evidence

ORD record
ord-2a432b35f1d5454384d64775d49107f5
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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