Dichloromethane → 2-Chloro-5-iodobenzaldehyde

HRID 602058ノート

反応式

HRID 602058 の反応式
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]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 671539432-Chloro-5-iodobenzyl alcoholHCID 178418287HCID 178418287、化合物

生成物 1

HCID 221152692-Chloro-5-iodobenzaldehyde収率 67%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-212cfaf3c2f640db8ebeb4e873cca89c
出典データセット
uspto-grants-2011_03
特許番号
US07902394B2

反応ノート

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