Potassium Phosphate, Tribasic → 2-Chloro-4-cyclopropyl-5-methyl-6-fluoroaniline

HRID 1270734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270734
[Cl:1][C:2]1[CH:8]=[C:7](Br)[C:6]([CH3:10])=[C:5]([F:11])[C:3]=1[NH2:4].[CH:12]1(B(O)O)[CH2:14][CH2:13]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>COCCOC.O>[Cl:1][C:2]1[CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[C:6]([CH3:10])=[C:5]([F:11])[C:3]=1[NH2:4]

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 184515002-Chloro-4-bromo-5-methyl-6-fluoroaniline

Produkt 1

HCID 184515032-Chloro-4-cyclopropyl-5-methyl-6-fluoroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Versuchsvorschrift

2-Chloro-4-bromo-5-methyl-6-fluoroaniline (6.5 g, 27 mmol), cyclopropylboronic acid (2.8 g, 33 mmol), tetrakis (triphenylphosphine)palladium (0) (1.4 g, 1.3 mmol), potassium phosphate (20.2 g, 95 mmol) and tricyclohexylphosphine (0.77 g, 2.7 mmol) are combined and stirred in 200 mL of a 4:1 DME/water solution. The mixture is degassed by repeated alternating application of vacuum and positive nitrogen pressure (10×). The mixture is heated to reflux temperature for 2 days and then cooled to room temperature. Most of the DME is removed by rotary evaporator and the residual mixture is partitioned between Et2O (250 mL) and water (250 mL). The organic phase is washed with brine (3×250 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude product is purified using flash chromatography (8% CH2Cl2/hexanes) to give 2-chloro-4-cyclopropyl-5-methyl-6-fluoroaniline as a tan oil.

Aufarbeitung

  1. customThe mixture is degassed by repeated alternating application of vacuum and positive nitrogen pressure (10×)
  2. temperatureThe mixture is heated
  3. temperatureto reflux temperature for 2 days
  4. customMost of the DME is removed by rotary evaporator
  5. customthe residual mixture is partitioned between Et2O (250 mL) and water (250 mL)
  6. washThe organic phase is washed with brine (3×250 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated by rotary evaporator
  9. customThe crude product is purified

Quellen und Nachweise

ORD-Eintrag
ord-2baa8c18e5704287afaadc91bd50569f
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202364B2

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