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1,2-Dibromoethane → HCID 66922349, Verbindung

HRID 2039837
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2039837
BrCCBr.[F:5][C:6]1[C:7]([CH3:14])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9]Br.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]([C:30]2[C:34]3[CH:35]=[N:36][C:37]([O:39][CH3:40])=[CH:38][C:33]=3[N:32]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:31]=2Cl)=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1COCC1.CCCCCC.[Zn].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.Cl[Si](C)(C)C.CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]([C:30]2[C:34]3[CH:35]=[N:36][C:37]([O:39][CH3:40])=[CH:38][C:33]=3[N:32]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:31]=2[CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([F:5])[C:7]=2[CH3:14])=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 4

HCID 78391,2-DibromoethaneHCID 27792443-Fluoro-2-methylbenzyl bromideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66922140HCID 66922140, Verbindung

Produkt 1

HCID 66922349HCID 66922349, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 6397ChlorotrimethylsilaneKatalysator
HCID 23994ZincKatalysator
HCID 167845palladium(II) acetateKatalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To zinc (167 mg, 2.55 mmol) in dry THF (500 μl) in a dry flask under an argon atmosphere was added 1,2-dibromoethane (5.49 μl, 63.7 μmol). The mixture was heated three times to reflux with a heat gun and allowed to cool to room temperature. Then chlorotrimethylsilane (0.27 μl, 2.12 μmol) was added and the mixture was stirred at room temperature for 20 min. Subsequently the flask was placed in an ice bath and a solution of 3-fluoro-2-methyl-benzylbromide (259 mg, 1.27 mmol) in dry THF (1 ml) was added slowly so that the temperature remained at 0° C. The mixture was stirred at 0° C. for 4.5 h and placed in the refrigerator overnight. Then the cooled mixture was added dropwise to a precooled solution (−78° C.) of B-OM-9-BBN (2.12 ml, 2.12 mmol, 1 M) in hexane. The mixture was stirred at room temperature for 30 min. DMF (5 ml) was added, followed by the compound of step 6 (100 mg, 212 μmol), palladium(II) acetate (4.77 mg, 21.2 μmol) and S—PHOS (17.4 mg, 42.5 μmol). The reaction mixture was stirred at 100° C. for 3 h. After cooling, the mixture was quenched with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (EA (10 to 60%) HEP) to give 90 mg of the title compound.

Aufarbeitung

  1. temperatureThe mixture was heated three times
  2. temperatureto reflux with a heat gun
  3. customSubsequently the flask was placed in an ice bath
  4. customremained at 0° C
  5. stirringThe mixture was stirred at 0° C. for 4.5 h
  6. customplaced in the refrigerator overnight
  7. stirringThe mixture was stirred at room temperature for 30 min
  8. stirringThe reaction mixture was stirred at 100° C. for 3 h
  9. temperatureAfter cooling
  10. customthe mixture was quenched with water
  11. extractionextracted with EA
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. filtrationfiltered
  14. customevaporated under reduced pressure
  15. customThe residue was purified by silica gel chromatography (EA (10 to 60%) HEP)

Quellen und Nachweise

ORD-Eintrag
ord-7e8688ad9c5a45f1ad2a21b30b725962
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580813B2

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