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Potassium Carbonate → tert-Butyl 4-(3,3,3-trifluoroprop-1-en-2-yl)phenylcarbamate

HRID 2197598
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2197598
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)CC(C)OB([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])O1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:33][C:32]([F:35])([F:34])[C:30]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1)=[CH2:31]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27736084-Bromoaniline, N-BOC protectedHCID 164142704,4,6-Trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane2×

Produkt 1

HCID 86630282tert-Butyl 4-(3,3,3-trifluoroprop-1-en-2-yl)phenylcarbamateAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Versuchsvorschrift

To a mixture of tert-butyl 4-bromophenylcarbamate (1.67 g, 6.14 mmol), potassium carbonate (3.38 g, 24.46 mmol), and tetrakis(triphenylphosphine)palladium (365 mg, 0.316 mmol), was added 4,4,6-trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane (1.64 g, 7.39 mmol), and degassed 1,2-dimethoxyethane (40 mL) and water (20 mL). The mixture for refluxed for 2 hours, cooled to ambient temperature, added more of 4,4,6-trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane (475 mg, 2.14 mmol) and tetrakis(triphenylphosphine)palladium-(189 mg, 0.164 mmol), and refluxed for 5 hours. The reaction mixture was cooled to room temperature, filtered, diluted with water (200 mL), extracted twice with ethyl acetate (200 mL), washed with brine, dried (Na2SO4) and concentrated to an orange oil. The residue was purified by silica gel chromatography (AnaLogix® SF25-40G; 50 micron silica; eluted with 0-15% ethyl acetate in hexane at 30 mL/min) to provide the title compound (1.223 g, 4.26 mmol, 69.4% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.53 (s, 1H), 7.52 (d, J=8.8, 2H), 7.40 (d, J=8.4, 2H), 6.03-5.99 (m, 1H), 5.97-5.94 (m, 1H), 1.48 (s, 9H); MS (DCI/NH3) m/e 305 (M+NH4)+.

Aufarbeitung

  1. customdegassed 1,2-dimethoxyethane (40 mL) and water (20 mL)
  2. temperatureThe mixture for refluxed for 2 hours
  3. temperaturerefluxed for 5 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationfiltered
  6. additiondiluted with water (200 mL)
  7. extractionextracted twice with ethyl acetate (200 mL)
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated to an orange oil
  11. customThe residue was purified by silica gel chromatography (AnaLogix® SF25-40G; 50 micron silica; eluted with 0-15% ethyl acetate in hexane at 30 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-f3209763d32641529df0eaa50ca3ca31
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08338603B2

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