3-[3-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoic Acid → 3-[3-Fluoro-4-(trifluoromethyl)phenyl]propionic acid

HRID 1844040Notes

Reaction equation

HRID 1844040 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]>CO.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 1

HCID 27375813-[3-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoic Acid

Product 1

HCID 467374883-[3-Fluoro-4-(trifluoromethyl)phenyl]propionic acidYield 81.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

10% NIX was added to a stirred solution of 3-(3-fluoro-4-(trifluoromethyl)phenyl)-acrylic acid (I-77a: 5.5 g, 0.0234 mol) in methanol. The resulting mixture was stirred under hydrogen atmosphere for 4 hours. The reaction was monitored by TLC (5% methanol in CHCl3). The catalyst was filtered through celite bed and the solvent distilled under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 4.5 g of the product (81.8% yield).

Workup

  1. filtrationThe catalyst was filtered through celite bed
  2. distillationthe solvent distilled under reduced pressure
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-952d023f73f04fedab2c6da7a5e6b182
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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