Triethylamine → tert-Butyl (4-bromo-2-methylphenyl)carbamate

HRID 32794

Reaktionsgleichung

Reaktionsgleichung von HRID 32794
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.CCN(CC)CC.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.[NH4+].[Cl-]>O1CCOCC1.O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:17])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:4]([CH3:9])[CH:3]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 114234-Bromo-2-methylanilineHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 2735638tert-Butyl (4-bromo-2-methylphenyl)carbamateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r.t., were added Et3N (2.7 mL, 1.2 eq) and BOC2O (4.2 g, 1.2 eq). The reaction mixture was stirred at r.t. for 96 hr. Sat.aq. NH4Cl and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2×20 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH)) to give the title compound as a white solid (1.22 g, 79%).

Aufarbeitung

  1. customthe phases were separated
  2. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  4. filtrationthe solids were filtered
  5. customthe solvent evaporated
  6. customThe residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH))

Quellen und Nachweise

ORD-Eintrag
ord-fa511c497d154a0b80b25451fc45b008
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427630B2

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