(Dimethyl sulfide)trihydroboron → 7-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 473950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473950
CSC.B.[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14][C:13](=O)[CH:12]([CH3:16])[O:11][C:10]=2[CH:17]=1>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14][CH2:13][CH:12]([CH3:16])[O:11][C:10]=2[CH:17]=1

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 226231297-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Produkt 1

HCID 580646527-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Borane dimethyl sulfide complex (2 M solution in THF, 0.414 mL, 0.828 mmol) was added at room temperature to a solution of 7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one A-2 (100.0 mg, 0.414 mmol) in anhydrous THF (4.10 mL) under an atmosphere of argon. The reaction mixture was heated to reflux for 2 h, cooled to room temperature, quenched with methanol (1.0 mL), stirred for 30 mins and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give 7-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine A-3 (92.9 mg, Yield=98%). MS (ESI) [M+1]+ 228, 230.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customquenched with methanol (1.0 mL)
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-4bd088a2df78400c96fb6b17f6be98a5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637507B2

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