Sulfuric Acid → 2-Bromomethylphenylacetic acid t-butyl ester

HRID 397475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397475
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH3:18][C:19](=[CH2:21])[CH3:20].C(=O)(O)[O-].[Na+]>O1CCOCC1.COC(C)(C)C>[C:19]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][Br:1])([CH3:21])([CH3:20])[CH3:18]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 12889260[2-(Bromomethyl)phenyl]acetic acid

Produkt 1

HCID 590858792-Bromomethylphenylacetic acid t-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15413tert-Butyl methyl etherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a solution of 80 g (0.349 mol) 2-bromomethylphenylacetic acid in 700 mL 1,4-dioxane in a 2 L heavy-walled flask was added 84 mL (1.571 mol) concentrated sulfuric acid at ambient temperature. The reaction mixture was chilled to −15° C., and 580 mL isobutylene was condensed directly into the reaction vessel. The sealed pressure flask was shaken mechanically at room temperature for 4 h (the pressure inside the flask rises to ca. 20 psi during this step). The mixture was carefully quenched by slowly pouring it into a 0-5° C. stirred mixture of 1.2 L tert-butyl methyl ether and 336 g (4.0 mol) solid sodium bicarbonate before slow dilution with 1.2 L ice-water. The separated organic phase was washed with 0.8 L brine, dried with sodium sulfate, filtered concentrated in vacuo to give an oil, which was used without further purification.

Aufarbeitung

  1. customcondensed directly into the reaction vessel
  2. customThe mixture was carefully quenched
  3. additionby slowly pouring it into a 0-5° C.
  4. stirringstirred
  5. washThe separated organic phase was washed with 0.8 L brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil, which
  10. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-7e5bab0db56749dea4088df587c46272
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610701B2

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