Boron tribromide → N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide

HRID 890756

Reaktionsgleichung

Reaktionsgleichung von HRID 890756
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17]>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 6465664N-[2-(2-methoxyphenyl)ethyl]methanesulfonamide

Produkt 1

HCID 22246821N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamideAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Boron tribromide (1.0 M in CH2Cl2, 80.8 mL, 80.8 mmol) was added to a solution of N-[2-(2-methoxy-phenyl)-ethyl]-methanesulfonamide (18.5 g, 80.8 mmol) in CH2Cl2 (200 mL). The reaction was stirred at room temperature for 2 h and was poured onto water (200 mL). The aqueous layer was extracted with CH2Cl2 (2×) and the organic solution was washed with water (1×) and aqueous NaHCO3 (satd, 1×). The organic solution was dried over MgSO4, filtered, and concentrated to afford N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide (16.8 g). 1H NMR (400 MHz, CDCl3) δ 7.11 (m, 2H), 6.86 (m, 1H), 6.80 (m, 1H), 4.79 (m, 1H), 3.39 (t, 2H), 2.88 (t, 2H), 2.77 (s, 3H).

Aufarbeitung

  1. additionwas poured onto water (200 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  3. washthe organic solution was washed with water (1×) and aqueous NaHCO3 (satd, 1×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81ab01c9149644da83ee00b49a2ffef9
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998423B2

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