Boron tribromide → 2-(2-Hydroxy-4-nitrophenyl)benzothiazole

HRID 339497

Reaktionsgleichung

Reaktionsgleichung von HRID 339497
C[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 672372802-(2-Methoxy-4-nitrophenyl)benzothiazole

Produkt 1

HCID 1360605262-(2-Hydroxy-4-nitrophenyl)benzothiazoleAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared as described in the Demethylation section above using 2-(2-methoxy-4-nitrophenyl)benzothiazole (0.5 g, 1.75 mmol) in dry DCM (30 ml) was added dropwise at room temperature and BBr3 (1.0 M solution in DCM, 8.8 ml, 8.8 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched by addition of MeOH (5 ml) and extracted with 8% w/v NaOH (5×35 ml). The combined aqueous extracts were acidified with 6 M HCl and extracted with EtOAc (3×70 ml). The combined organic extracts were washed with brine (40 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give a solid which was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.47 g, 99%) as a pale yellow solid after work-up and flash chromatography (1:1 Hexane/EtOAc).

Aufarbeitung

  1. customPrepared
  2. additionwas added dropwise at room temperature
  3. customThe reaction was quenched by addition of MeOH (5 ml)
  4. extractionextracted with 8% w/v NaOH (5×35 ml)
  5. extractionextracted with EtOAc (3×70 ml)
  6. washThe combined organic extracts were washed with brine (40 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed under reduced pressure
  9. customto give a solid which
  10. customwas purified by flash chromatography (1:1 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6703bc673ec8421abc37a13bb0317d19
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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