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Sulfuric Acid → 2-Trifluoroacetyl-4-tert-butylanisole

HRID 1389561
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HRID 1389561 반응식
[Mg].I[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[O:13][CH3:14].[F:15][C:16]([F:21])([F:20])[C:17](O)=[O:18].S(=O)(=O)(O)O>C(OCC)C>[F:15][C:16]([F:21])([F:20])[C:17]([C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[O:13][CH3:14])=[O:18]
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참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 5462224MagnesiumHCID 149144624-Tert-butyl-2-iodo-1-methoxybenzene

생성물 1

HCID 202969942-Trifluoroacetyl-4-tert-butylanisole

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

To 0.73 g of magnesium suspended in 5 ml of diethyl ether were added dropwise, under nitrogen, 8.70 g of 2-iodo-4-tert-butylanisole [described in Reference Example 1(a)] dissolved in 15 ml of diethyl ether and heated at reflux for one hour. To this solution were added dropwise 0.74 ml of trifluoroacetic acid dissolved in 3 ml of diethyl ether at room temperature, and heated at reflux for 1.5 hours. The reaction mixture was poured into ice-water, acidified with conc. sulfuric acid and extracted with diethyl ether. The extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and cyclohexane (1:2) as an eluting agent to give 1.83 g of the title compound having the following physical properties as pale yellow oil.

후처리

  1. additionwere added dropwise, under nitrogen
  2. temperatureheated
  3. temperatureat reflux for one hour
  4. temperatureheated
  5. temperatureat reflux for 1.5 hours
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with water and saturated brine successively
  8. dry with materialdried over magnesium sulfate anhydride
  9. concentrationconcentrated at reduced pressure
  10. customThe residue was chromatographed on silica gel column

출처 및 근거

ORD 기록
ord-5e76ed1f017943c980ad6ef44f192297
출처 데이터셋
uspto-grants-1981_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04245099

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