Formic Acid → 4-Fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetic acid

HRID 22193

반응식

HRID 22193 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.C(O)=O.CS(O)(=O)=O.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 962WaterHCID 6395Methanesulfonic AcidHCID 19927552Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetate

생성물 1

HCID 199275564-Fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetic acid수율 95.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The crude ester from Step B (5.3 g, 16 mmole) was combined with 20 ml of 88% formic acid and 2.1 ml (33 mmole) of methane sulfonic acid. The emulsion was refluxed for five hours during which time it gradually became homogeneous. After cooling, water and methylene chloride were added and the aqueous phase was separated and extracted twice with methylene chloride. The organic phases were combined, dried (MgSO4) and concentrated. The crude residue was taken up in 4% ethyl acetate/hexane and filtered through a plug of silica gel to remove nonpolar impurities. The product acid was then rinsed from the silica gel with ethyl acetate and the solvent concentrated. The acid was a colorless solid (4.5 g, 95% yield). 1H NMR (CDCl3) δ: 10.05 (1H, br s), 7.20 (5H, m), 7.03 (3H, m), 3.81 (1H, dd, J=6, 8 Hz), 3.57 (1H, m), 3.23 (1H, dd, J= 6, 12 Hz).

후처리

  1. temperatureThe emulsion was refluxed for five hours during which time it gradually became homogeneous
  2. temperatureAfter cooling
  3. customthe aqueous phase was separated
  4. extractionextracted twice with methylene chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. filtrationfiltered through a plug of silica gel
  8. customto remove nonpolar impurities
  9. washThe product acid was then rinsed from the silica gel with ethyl acetate
  10. concentrationthe solvent concentrated

출처 및 근거

ORD 기록
ord-8483dd164cf14465bb793c280b8948c3
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428027

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