Dichloromethane → 2-Chloro-5-iodobenzaldehyde

HRID 602058노트

반응식

HRID 602058 반응식
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH2:12][OH:13].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>CCOCC>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH:12]=[O:13]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 671539432-Chloro-5-iodobenzyl alcoholHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 221152692-Chloro-5-iodobenzaldehyde수율 67%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A methylene chloride solution (99 mL) of (2-chloro-5-iodophenyl)methanol (9.01 g, 33.5 mmol) and PCC (8.67 g, 40.2 mmol) were combined and stirred at rt. After 16 h, Et2O was added and the solution stirred for 30 minutes. The solution was then filtered and the organic layer was washed with H2O (2×), NaHCO3 (3×), and brine. The organic layer was dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-20% EtOAc/hexanes) to afford 5.94 g of product (67%). 1H NMR (400 MHz, chloroform-d) δ ppm 10.38 (s, 1 H) 8.22 (d, J=2.02 Hz, 1 H) 7.83 (dd, J=8.46, 2.15 Hz, 1 H) 7.21 (d, J=8.59 Hz, 1 H).

후처리

  1. stirringthe solution stirred for 30 minutes
  2. filtrationThe solution was then filtered
  3. washthe organic layer was washed with H2O (2×), NaHCO3 (3×), and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by Biotage chromatography (0%-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-212cfaf3c2f640db8ebeb4e873cca89c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902394B2

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