Pyridiniumtribromide → 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

HRID 1413017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1413017
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[CH:15]=[C:14]4[CH2:17][CH2:18][CH2:19][C:20](=[O:21])[C:13]4=[CH:12][C:11]=3[O:10][CH2:9][C:8]=2[CH:22]=1)(=[O:3])[CH3:2].C(Cl)Cl.CO.[Br-:28].[Br-:29].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CCOC(C)=O>[Br:28][CH:19]1[CH2:18][CH2:17][C:14]2=[CH:15][C:16]3[C:7]4[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH2:2][Br:29])=[CH:22][C:8]=4[CH2:9][O:10][C:11]=3[CH:12]=[C:13]2[C:20]1=[O:21]

Komponenten

5

Edukt 3

HCID 21124087PyridiniumtribromideHCID 21226129Dichloromethane methanolHCID 866883753-acetyl-10,11-dihydro-5H-dibenzo(c,g)chromen-8(9H)-one

Produkt 1

HCID 866883729-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A 20 mL vial with a stir bar was charged with 3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (100 mg, 0.366 mmol), 9:1 CH2Cl2/MeOH (3.4 mL) and pyridinium tribromide (246 mg, 0.769 mmol). The solution was heated to 35° C. After 30 minutes, the reaction was judged complete. The mixture was cooled to ambient temperature, diluted with EtOAc (50 mL) and sequentially washed with saturated aqueous Na2S2O3 (20 mL), 2% aqueous NaHCO3 (20 mL), water (20 mL), and brine (10 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure resulting in 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (68 mg, 41%): 400 MHz 1H NMR (CDCl3) δ 8.03-8.01 (m, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.82 (s, 1H), 7.71 (s, 1H), 7.67 (s, 1H), 5.19 (s, 2H), 4.74 (dd, J=4.1, 4.1 Hz, 1H), 4.45 (s, 2H), 3.37-3.29 (m, 1H), 2.99-2.92 (m, 1H), 2.59-2.46 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. washsequentially washed with saturated aqueous Na2S2O3 (20 mL), 2% aqueous NaHCO3 (20 mL), water (20 mL), and brine (10 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customresulting in 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (68 mg, 41%)

Quellen und Nachweise

ORD-Eintrag
ord-c7c64b456eb84242b4067a9090b178d8
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921341B2

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