Hydrochloric Acid → 2-Iodo-9,10-dihydrophenanthrene

HRID 68493ノート

反応式

HRID 68493 の反応式
N[C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.Cl.N([O-])=O.[Na+].[I-:21].[K+]>ClCCl.C(O)(=O)C>[I:21][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 4071852-Amino-9,10-dihydrophenanthreneHCID 23668193Sodium Nitrite

生成物 1

HCID 576345402-Iodo-9,10-dihydrophenanthrene収率 62%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Under an argon atmosphere, 220 g of 2-amino-9,10-dihydrophenanthrene, 3 L of 3N HCl, and 2 L of acetic acid were added, and then the mixture was stirred for 3 hours under heat. After having been cooled to room temperature, the mixture was cooled with ice, and then an aqueous solution of 91 g of sodium nitrite was dropped to the mixture. After the resultant mixture had been stirred for 1 hour under ice cooling, an aqueous solution of 660 g of potassium iodide was added to the mixture. Subsequently, 2 L of dichloromethane were added to the mixture, and then the whole was stirred at room temperature for 3 hours. After that, the mixture was extracted with dichloromethane. The organic layer was repeatedly washed with an aqueous solution of potassium carbonate, and was then dried with magnesium sulfate. After that, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 210 g of a pale yellow solid were obtained (in 62% yield).

後処理

  1. temperatureunder heat
  2. temperaturethe mixture was cooled with ice
  3. stirringthe whole was stirred at room temperature for 3 hours
  4. extractionAfter that, the mixture was extracted with dichloromethane
  5. washThe organic layer was repeatedly washed with an aqueous solution of potassium carbonate
  6. dry with materialwas then dried with magnesium sulfate
  7. customAfter that, the solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8360170e64be4ecaa652d3fdf39f2c94
出典データセット
uspto-grants-2014_09
特許番号
US08822041B2

反応ノート

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