Sulfuric Acid → 2-Chloro-4-fluoro-5-nitrotoluene

HRID 231435

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HRID 231435 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].S(=O)(=O)(O)O.[N+:15]([O-])([O-:17])=[O:16].[K+]>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][C:3]=1[CH3:9]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 967472-Chloro-4-fluorotoluene

생성물 1

HCID 101039792-Chloro-4-fluoro-5-nitrotoluene수율 49.7%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

To a mixture of 20.0 g (0.138 mole) of 2-chloro-4fluorotoluene in 50 ml of 1,2-dichloroethane which had been cooled to 0° C. was added 50 ml of concentrated sulfuric acid. While maintaining the temperature below 10° C., 14.0 g (0.138 mole) of potassium nitrate was added slowly to the mixture. After three hours the reaction mixture was poured into ice, and the resulting mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was passed through a silica gel column, eluting with heptane. Appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 13.0 g of 2-chloro-4-fluoro-5-nitrotoluene as a yellow solid. The nmr spectrum was consistent with the proposed structure.

후처리

  1. additionwas added slowly to the mixture
  2. additionAfter three hours the reaction mixture was poured into ice
  3. extractionthe resulting mixture was extracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. washeluting with heptane
  8. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-ae2b6f4c832b4099b29069b3827135d1
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04846882

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