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

HRID 2119246ノート

反応式

HRID 2119246 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad9d51402d8a41068ecf309517636482
出典データセット
uspto-grants-1987_07
特許番号
US04683314

反応ノート

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