Water → 2-(4-Bromo-2-methylphenyl)acetic acid

HRID 708856노트

반응식

HRID 708856 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH3:11])[CH:2]=C.I([O-])(=O)(=O)=[O:13].[Na+].[OH2:18]>C(Cl)(Cl)(Cl)Cl.C(#N)C.O.[Ru](Cl)(Cl)Cl>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][C:2]([OH:13])=[O:18])=[C:5]([CH3:11])[CH:6]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 23667635Sodium periodateHCID 534031561-Allyl-4-bromo-2-methylbenzene

생성물 1

HCID 190260522-(4-Bromo-2-methylphenyl)acetic acid수율 88%

시약·촉매·용매 3

HCID 6093376Ruthenium trichloride hydrate촉매HCID 5943Carbon Tetrachloride용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 16A (12 g, 56.8 mmol) in CCl4 (200 mL), acetonitrile (200 mL) and water (300 mL) at rt was added ruthenium (III) chloride hydrate (1.474 g, 7.11 mmol) and sodium periodate (48.6 g, 227 mmol). The suspension was stirred vigorously for 5.0 h. The solvent was removed under vacuum. The residue was filtered though wet CELITE®, washed with EtOAc. The mixture was further extracted with EtOAc (3×400 mL). The volume of organic layers was reduced to ca 500 mL, washed with sat. sodium sulfite/with conc. HCl (pH ca 2-3). The organic layer was dried over sodium sulfate and concentrated. After evaporation of solvent, 16B (11.47 g, 50.1 mmol, 88% yield) was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.27 (s, 3H) 3.60 (s, 2H) 7.04 (d, J=7.91 Hz, 1H) 7.28 (dd, J=8.13, 1.98 Hz, 1H) 7.32 (s, 1H).

후처리

  1. customThe solvent was removed under vacuum
  2. filtrationThe residue was filtered though wet CELITE®
  3. washwashed with EtOAc
  4. extractionThe mixture was further extracted with EtOAc (3×400 mL)
  5. washwashed with sat. sodium sulfite/with conc. HCl (pH ca 2-3)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customAfter evaporation of solvent

출처 및 근거

ORD 기록
ord-c7c123501fae4b4f829a461ac3c66e83
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174974B2

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