Boron tribromide → Ethyl 3-(1-(4-bromobenzyl)-6-hydroxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

HRID 1527755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527755
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16]C)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][CH:3]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:18][C:19]([CH3:25])([CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 90410153ethyl 3-(1-(4-bromobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

Produkt 1

HCID 90411063Ethyl 3-(1-(4-bromobenzyl)-6-hydroxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of ethyl 3-(1-(4-bromobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (12 g, 27 mmol) in DCM (200 mL) was added BBr3 (20 g, 81 mmol) in DCM (100 mL) drop wise at −78° Celsius. The solution was gradually warmed to 5° Celsius and stirred for 3 h. The reaction mixture was slowly added to saturated NaHCO3 with rapid stirring for 1 h. The organic phase was separated and aqueous phase was extracted with DCM (200 mL). The combined organic phases were dried over Na2SO4, filtered, concentrated to dryness and purified by FCC to provide the title compound. MS (ESI): mass calcd. for C21H23BrN2O3, 430.09; m/z found, 438 [M+H]+.

Aufarbeitung

  1. stirringwith rapid stirring for 1 h
  2. customThe organic phase was separated
  3. extractionaqueous phase was extracted with DCM (200 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. custompurified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-37bb20d2b0714de9bd7e3b6ea057bb7b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089569B2

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