Boron tribromide → 4-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol

HRID 1891363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891363
[Br:1][C:2]1[C:3]([Cl:24])=[CH:4][C:5]([O:22]C)=[C:6]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:24])=[CH:4][C:5]([OH:22])=[C:6]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])[CH:7]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 684691311-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Produkt 1

HCID 684721004-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenolAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of DCM (25.0 mL) containing 1-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine (2.15 g, 5 mmol) at −78° C. was added BBr3 (12.5 mL, 1M in DCM, 12.5 mmol) dropwise. The mixture was gradually warmed to rt while it was stirred for 4 hrs. The mixture was concentrated and partitioned between ethyl acetate (100 mL) and sat. NaHCO3 solution (100 mL). The organic layer was further washed with brine (2×50 mL), dried over MgSO4, and evaporated. The purification of the crude material by silica gel column chromatography eluting with hexane/ethyl acetate (6/1) yielded 4-bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol as a white solid (1.9 g). NMR (CDCl3), δ, 7.739 (1H, s), 7.186-7.259 (4H, m), 7.127 (1H, s), 3.692 (2H, m), 2.502-2.539 (2H, m), 1.802-1.868 (2H, m), 1.601-1.676 (2H, m).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate (100 mL) and sat. NaHCO3 solution (100 mL)
  3. washThe organic layer was further washed with brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe purification of the crude material by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (6/1)

Quellen und Nachweise

ORD-Eintrag
ord-a8e28e40db674c1283421551010dce52
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507536B2

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