Dichloromethane → HCID 69991466, Verbindung

HRID 1250118

Reaktionsgleichung

Reaktionsgleichung von HRID 1250118
B1(B2C3CCCC2CCC3)C2CCCC1CCC2.C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH:43]=[CH2:44].ClCCl.[Br:49][C:50]1[CH:55]=[CH:54][CH:53]=[C:52](Br)[CH:51]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.[Pd](Cl)Cl.O.CN(C)C=O>[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH2:43][CH2:44][C:52]1[CH:53]=[CH:54][CH:55]=[C:50]([Br:49])[CH:51]=1

Komponenten

10

Edukt 5

HCID 6344DichloromethaneHCID 79271,3-DibromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 77314Methyl 3-butenoateHCID 113224419-Borabicyclo[3.3.1]nonane dimer

Produkt 1

HCID 69991466HCID 69991466, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24290Palladium ChlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[9-Borabicyclo[3.3.1]nonane dimer] (13.4 mL, 6.68 mmol) (9-BBN dimer) was added to a solution of methyl-3-butenoate (0.71 mL, 6.68 mmol) in tetrahydrofuran (2.7 mL) at 0-5° C. under an argon atmosphere, and the mixture was stirred for 4 hours. N,N-Dimethylformamide (27 mL), palladium(II) chloride, dichloromethane (130 g, 0.16 mmol), 1,3-dibromobenzene (0.77 mL, 61.37 mmol) and potassium phosphate (powdered, 1.5 g, 6.94 mmol) were added. The mixture was treated at 50° C. overnight. Water was added and the mixture extracted with diethyl ether. The extract was washed with water, brine, and dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate) gave 4-(3-bromophenyl)butyric acid methyl ester as a clear oil (0.26 mg, 16%).

Aufarbeitung

  1. additionThe mixture was treated at 50° C. overnight
  2. extractionthe mixture extracted with diethyl ether
  3. washThe extract was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f2d14f1a6ab046f4bbd61fa0d584cbdd
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335459B1

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