Sulfuric Acid → 1-Chloro-3-iodo-5-nitrobenzene

HRID 326643ノート

反応式

HRID 326643 の反応式
[Cl:1][C:2]1[C:8]([N+]([O-])=O)=[CH:7][C:5](N)=[C:4]([I:12])[CH:3]=1.S(=O)(=O)(O)O.[N:18]([O-:20])=[O:19].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([I:12])[CH:5]=[C:7]([N+:18]([O-:20])=[O:19])[CH:8]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 15739203HCID 15739203、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 197351701-Chloro-3-iodo-5-nitrobenzene収率 42.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4-chloro-2-iodo-5-nitroaniline (8.5 g) in ethanol (38 ml) was added concentrated sulphuric acid (4.4 ml) dropwise, then the solution was heated to reflux and solid sodium nitrite (4.9 g) added in small amounts over 30 minutes. The mixture was refluxed a further one hour and poured into ice water, the product extracted into ethyl acetate, washed with water and brine and the organic layer was dried over sodium sulfate. The solution was evaporated and the residue purified by column chromatography to give 5-chloro-3-iodonitrobenzene (3.4 g). δ (360 MHz, DMSO-d6) 8.28 (1H, d, 2-H), 8.35 (1H, d, 6-H) and 8.46 (1H, d, 4-H).

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed a further one hour
  4. extractionthe product extracted into ethyl acetate
  5. washwashed with water and brine
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customThe solution was evaporated
  8. customthe residue purified by column chromatography

出典と根拠

ORDレコード
ord-d12b293ebc7d45f99707c434da6840af
出典データセット
uspto-grants-1993_12
特許番号
US05270309

反応ノート

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