Triphosgene → 6-Bromo-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 44190

Reaktionsgleichung

Reaktionsgleichung von HRID 44190
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][OH:10].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:12](=[O:14])[O:10][CH2:9][C:3]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 94429TriphosgeneHCID 110308742-Amino-5-bromobenzenemethanol

Produkt 1

HCID 259189636-Bromo-1,4-dihydro-2H-3,1-benzoxazin-2-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2-amino-5-bromophenyl)methanol (772 mg, 3.8 mmol) in 15 ml THF was added triphosgene (1.03 g, 3.8 mmol) under nitrogen. After precipitation of a colorless solid, stirring was continued for 20 min before water was added. The solution was extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated, affording 6-bromo-1H-benzo[d][1,3]oxazin-2(4H)-one (830 mg, 3.64 mmol, 96%) as colorless solid.

Aufarbeitung

  1. customAfter precipitation of a colorless solid
  2. additionwas added
  3. extractionThe solution was extracted several times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-832a93207d004a2982842647434dcf26
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541404B2

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