Sulfuric Acid → 3-(3,5-Difluorophenyl)propionic acid

HRID 13690

반응식

HRID 13690 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:10]=[C:11]([F:13])[CH:12]=1

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 5228103-(3,5-Difluorophenyl)acrylic acid

생성물 1

HCID 36694983-(3,5-Difluorophenyl)propionic acid수율 92.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

Hydrogenate a mixture of 3,5-difluorocinnamic acid (10.0 g, 54.3 mmol), 5% palladium on carbon (1.5 g), and concentrated sulfuric acid (10 ml) in tetrahydrofuran (195 ml) at 60 psi at room temperature overnight. After filtering the catalyst, dilute with ether, wash with water twice, dry over anhydrous sodium sulfate, and concentrate to obtain the title compound as clear colorless crystals (9.32 g, 92%). NMR (400 MHz, CDCl3): δ 2.67 (t, 2H), 2.94 (t, 2H), 6.65 (t, 1H), 6.74 (d, 2H).

후처리

  1. filtrationAfter filtering the catalyst
  2. additiondilute with ether
  3. washwash with water twice
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate

출처 및 근거

ORD 기록
ord-53d1feeb0cf9479f8fdc097813fafe67
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728150B2

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