m-Chloroperbenzoic acid → (4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxide

HRID 2119246노트

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HRID 2119246 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=2[CH2:27][S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:15][C:14]=1[CH3:35]>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=2[CH2:27][S:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:9])=[CH:15][C:14]=1[CH3:35]

참가 물질

3

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 13316982(4'-Fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-YL)methyl phenyl sulfide

생성물 1

HCID 13316983(4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxide수율 88%

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온도
-78 °C

실험 절차

m-Chloroperbenzoic acid (tech. grade, approximately 75% peroxide; 1.19 g, approximately 5 mmoles) was added in small portions to a stirred solution of (4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfide (1.68 g, 5 mmoles) at -78° C. The reaction mixture was then stirred at -78° C. for 30 minutes and allowed to warm to room temperature. The solution of the product was separated by filtration from the 3-chlorobenzoic acid which was washed with methylene chloride. The combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml then washed with dilute sodium hydroxide solution (2×50 ml) dried (MgSO4), filtered, and the solvent was evaporated in vacuo to leave 1.7 g of crude product. This was purified by flash chromatography on silica gel using a 40×150 mm column eluting with 3.5% (v:v) acetone in methylene chloride to give 1.55 g of the title compound as a gum. Dry toluene was added and evaporated in vacuo four times to dry the product, which then crystallized, m.p. 75°-85° C.

후처리

  1. temperatureto warm to room temperature
  2. customThe solution of the product was separated by filtration from the 3-chlorobenzoic acid which
  3. washwas washed with methylene chloride
  4. additionThe combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml
  5. washthen washed with dilute sodium hydroxide solution (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo
  9. customto leave 1.7 g of crude product
  10. customThis was purified by flash chromatography on silica gel using a 40×150 mm column
  11. washeluting with 3.5% (v:v) acetone in methylene chloride

출처 및 근거

ORD 기록
ord-ad9d51402d8a41068ecf309517636482
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04683314

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