Iodine → 2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol

HRID 1830531

반응식

HRID 1830531 반응식
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1.C([O-])(O)=O.[Na+].[I:16]I.OS([O-])(=O)=O.[Na+]>O>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([I:16])[CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 114237422-Chloro-6-(hydroxymethyl)-3-pyridinol

생성물 1

HCID 106845682-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol수율 62%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

C1 (11.6 g, 72.7 mmol) and NaHCO3 (18.3 g, 218 mmol) are added to 200 mL water. The mixture is stirred until homogeneous, the flask is placed in an ice bath, iodine (19.4 g, 76.3 mmol) is added, and the reaction is stirred over the weekend at rt. The pH of the mixture is adjusted to 3 with 2N NaHSO4, and the mixture is extracted with 4×50 mL EtOAc. The combined organic layer is dried over anhydrous MgSO4, is filtered, and the filtrate is concentrated in vacuo to a yellow solid. The crude solid is washed with EtOAc to provide 2-chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol (C2) as an off-white solid (62% yield), and the filtrate is concentrated to a small volume and is chromatographed over 250 g silica gel (230–400 mesh) eluting with 2.5:4.5:4:0.1 EtOAc/CH2Cl2/hexane/acetic acid. The fractions with the desired compound are combined and concentrated to afford additional pure C2 (12% yield). MS (EI) for C6H5ClINO2, m/z: 285(M)+.

후처리

  1. customis placed in an ice bath
  2. stirringthe reaction is stirred over the weekend at rt
  3. extractionthe mixture is extracted with 4×50 mL EtOAc
  4. dry with materialThe combined organic layer is dried over anhydrous MgSO4
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated in vacuo to a yellow solid
  7. washThe crude solid is washed with EtOAc

출처 및 근거

ORD 기록
ord-73120c1abefe4f30b7729776360b8a05
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067515B2

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