tert-Butanol → 4-t-butyl-2-fluoro-N-methoxycarbonylaniline

HRID 2116810

Reaktionsgleichung

Reaktionsgleichung von HRID 2116810
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[NH:4][C:5]([O:7][CH3:8])=[O:6].[C:13](O)([CH3:16])([CH3:15])[CH3:14].CCCCCC>S(=O)(=O)(O)O>[C:13]([C:11]1[CH:10]=[CH:9][C:3]([NH:4][C:5]([O:7][CH3:8])=[O:6])=[C:2]([F:1])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 6386tert-Butanol3×HCID 8058HexaneHCID 34841742-fluoro-N-methoxycarbonylaniline

Produkt 1

HCID 101050784-t-butyl-2-fluoro-N-methoxycarbonylanilineAusbeute 158,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-Fluoro-N-methoxycarbonylaniline (150 g, 0.859 mol) was dissolved in 77.6% sulfuric acid (206 g) to prepare a solution. t-Butyl alcohol (72.9 g, 1.07 mol) was added dropwise to the solution under a nitrogen atmosphere over a period of 30 min while stirring and heating the solution at 70° C. After the completion of the dropwise addition, the reaction solution was vigorously stirred at the same temperature for one hr. t-Butyl alcohol (72.9 g, 1.07 mol) was again added dropwise thereto over a period of 30 min. After the completion of the dropwise addition, the reaction solution was vigorously stirred at the same temperature for one hr. t-Butyl alcohol (72.9 g, 1.07 mol) was again added dropwise thereto over a period of 30 min. After the completion of the dropwise addition, the reaction solution was vigorously stirred at the same temperature for one hr. The reaction solution was cooled to room temperature. n-Hexane (530 mL) was then added to the cooled reaction solution to carry out extraction for separation of the mixture into a sulfuric acid layer and an organic layer. n-Hexane (530 mL) was again added to the sulfuric acid layer to carry out extraction for separation of an organic layer. The organic layers thus obtained were combined, and the combined organic layer was washed with water and saturated brine in that order. The solvent was then removed from the organic layer by distillation to give 307 g of 4-t-butyl-2-fluoro-N-methoxycarbonylaniline as an oily crude product (yield on weight basis 159%, purity as determined by gas chromatography 65.1%, 4-t-butyl form 5-t-butyl form=100:0).

Aufarbeitung

  1. customto prepare a solution
  2. additionAfter the completion of the dropwise addition
  3. stirringthe reaction solution was vigorously stirred at the same temperature for one hr
  4. additionAfter the completion of the dropwise addition
  5. stirringthe reaction solution was vigorously stirred at the same temperature for one hr
  6. waitover a period of 30 min
  7. additionAfter the completion of the dropwise addition
  8. stirringthe reaction solution was vigorously stirred at the same temperature for one hr
  9. temperatureThe reaction solution was cooled to room temperature
  10. extractionextraction
  11. customfor separation of the mixture into a sulfuric acid layer
  12. additionn-Hexane (530 mL) was again added to the sulfuric acid layer
  13. extractionextraction
  14. customfor separation of an organic layer
  15. customThe organic layers thus obtained
  16. washthe combined organic layer was washed with water and saturated brine in that order
  17. customThe solvent was then removed from the organic layer by distillation

Quellen und Nachweise

ORD-Eintrag
ord-f19e4b620c664f04b9c11e59920e2ed5
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439382B2

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