Water → 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone

HRID 1751529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751529
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)(=O)=O.C([Sn](CCCC)(CCCC)[C:33]([O:35]CC)=[CH2:34])CCC.O.[Br:47]N1C(=O)CCC1=O>CN(C)C=O.ClCCl.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:47][CH2:35][C:33]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)=[O:34]

Komponenten

8

Edukt 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 867087538-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate

Produkt 1

HCID 867087542-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanoneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate (780 mg, 1.7 mmol) and tributyl(1-ethoxyvinyl)stannane (0.86 mL, 2.6 mmol) in dimethylformamide was degassed with a stream of argon for 15 minutes. PdCl2(dppe) (50 mg, 0.086 mmol) was added and the reaction was stirred at room temperature. After 30 hours, water (1 mL) and N-bromosuccinimide (756 mg, 4.2 mmol) were sequentially added to the reaction. After stirring for 2.5 hours at room temperature the reaction was diluted with dichloromethane. The organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine. After the organic layer was dried (Na2SO4) and concentrated, the crude material was recrystallized from dichloromethane and hexanes to yield 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone (518 mg, 57%).

Aufarbeitung

  1. stirringAfter stirring for 2.5 hours at room temperature the reaction
  2. washThe organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine
  3. dry with materialAfter the organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe crude material was recrystallized from dichloromethane and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6f84fc2e1150415b8872acdfd91b5397
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156823B2

Notizen zur Reaktion

Wird geladen…