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

HRID 326643노트

반응식

HRID 326643 반응식
[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

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 15739203HCID 15739203, 화합물HCID 23668193Sodium Nitrite

생성물 1

HCID 197351701-Chloro-3-iodo-5-nitrobenzene수율 42.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d12b293ebc7d45f99707c434da6840af
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270309

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