1,3-Dibromo-5-chlorobenzene → 1-Bromo-3-chloro-5-cyclopropylbenzene

HRID 19789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19789
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[CH:10]1([Mg]Br)[CH2:12][CH2:11]1>C1COCC1.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>[Br:9][C:4]1[CH:3]=[C:2]([CH:10]2[CH2:12][CH2:11]2)[CH:7]=[C:6]([Cl:8])[CH:5]=1

Komponenten

5

Edukt 2

HCID 846761,3-Dibromo-5-chlorobenzeneHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 665209601-Bromo-3-chloro-5-cyclopropylbenzeneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1,3-dibromo-5-chlorobenzene (500 mg, 1.85 mmol) in THF (1 ml) was added cyclopropylmagnesium bromide (3698 μl, 0.5M solution in THF, 1.85 mmol) in a sealed tube and the reaction mixture was degassed with argon for 5 min before tetrakis(triphenylphosphine)palladium (0) (107 mg, 0.09 mmol) was added. The resulting solution was heated to 70° C. overnight, cooled to RT and then quenched with sat. NH4Cl solution and extracted with pentane. The organic phases were combined, washed with water and brine, dried over MgSO4 and filtered through a short pad of silica gel to give the desired product (272 mg, 64%) which did not require further purification. 1H NMR (CDCl3, 300 MHz): 7.28 (aptt, J=2.0 Hz, 1H), 7.08 (aptt, J=1.5 Hz, 1H), 6.97 (aptt, J=1.5 Hz, 1H), 1.83 (m, 1H), 1.04-0.97 (m, 2H), 0.72-0.67 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. temperaturecooled to RT
  3. customquenched with sat. NH4Cl solution
  4. extractionextracted with pentane
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a short pad of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2b7debaa34934d1abbc3bc7f4dd483ae
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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