Sulfuric Acid → 3,5-Dichloro-4-fluorobenzoic acid

HRID 39642노트

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HRID 39642 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5](Cl)=[O:6].ClC1C=C(C(F)(F)F)C=C(Cl)C=1F.S(=O)(=O)(O)[OH:27].ClS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5]([OH:27])=[O:6]

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 24638Chlorosulfonic acidHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-HCID 196123793,5-Dichloro-4-fluorobenzoyl chloride

생성물 1

HCID 199713033,5-Dichloro-4-fluorobenzoic acid수율 49%

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온도
80 °C

실험 절차

3,5-dichloro-4-fluorobenzoyl chloride can be prepared as follows: To a round bottom flask with nitrogen purge through a 10% aqueous NaOH trap, was added 3,5-dichloro-4-fluorobenzotriflouride (5.00 g, 21.46 mmol, Aldrich), concentrated sulfuric acid (4.30 g, 42.92 mmol), and finally chlorosulfonic acid (5.15 g, 43.78 mmol). The reaction began to bubble immediately. After the bubbling subsided, the mixture was heated to 80° C. for 1 hr, cooled to room temperature, and added cautiously to stirred ice water. This was extracted twice with methylene chloride. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to give a white solid (2.19 g) of 3,5-dichloro-4-fluorobenzoic acid in 49% yield. 1H-NMR (CD3COCD3, 300 MHz) δ (ppm): 7.95 (d, 2H).

후처리

  1. customTo a round bottom flask with nitrogen purge through a 10% aqueous NaOH trap
  2. customto bubble immediately
  3. temperaturecooled to room temperature
  4. additionadded cautiously
  5. extractionThis was extracted twice with methylene chloride
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-d2d63dcfc8f4419b85996138365541d8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524948B2

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