Triethylamine → 3-(4-Bromo-2-fluorobenzyl)-1,3-oxazolidin-2-one

HRID 500189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500189
[CH2:1]([O:4][C:5](Cl)=[O:6])[CH2:2]Cl.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[C:12]([F:18])[CH:11]=1.C(N(CC)CC)C.CC(C)([O-])C.[K+]>C1COCC1.C(Cl)Cl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:2][CH2:1][O:4][C:5]2=[O:6])=[C:12]([F:18])[CH:11]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 123052-Chloroethyl chloroformateHCID 184681974-Bromo-2-fluorobenzylamine hydrochlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 615319923-(4-Bromo-2-fluorobenzyl)-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-chloroethyl chloridocarbonate (114 μL, 1.1 mmol) was added to a mixture of 1-(4-bromo-2-fluorophenyl)methanamine hydrochloride (0.240 g, 1.0 mmol) and triethylamine (293 μL, 2.1 mmol). The mixture was stirred at RT for 3 h, and then 1M of potassium tert-butoxide in THF (1.2 mL) was added. The mixture was stirred overnight at RT, diluted with methylene chloride, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in next step without further purification. LCMS: (M+H)=275.9/273.9.

Aufarbeitung

  1. stirringThe mixture was stirred overnight at RT
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ca2163a1738a4d1ab56f09e44ee5ea8a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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