Boron tribromide → 2,4,6-Trichloropyrimidin-5-ol

HRID 334111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334111
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9]C)=[C:4]([Cl:11])[N:3]=1.B(Br)(Br)Br>C(Cl)Cl.CO.O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:11])[N:3]=1

Komponenten

6

Edukt 2

HCID 25134Boron tribromideHCID 202711362,4,6-Trichloro-5-methoxypyrimidine

Produkt 1

HCID 866673322,4,6-Trichloropyrimidin-5-olAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under an atmosphere of nitrogen a solution of 2,4,6-trichloro-5-methoxy-pyrimidine (4.0 g, 18.7 mmol) in DCM (200 mL) was cooled to 0° C. and treated with boron tribromide (neat, 6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at room temperature LCMS analysis indicated complete reaction. The reaction mixture was cooled and diluted with methanol (25 mL, CARE, EXOTHERM!) and the reaction mixture diluted with water (200 mL). The aqueous layer was washed with DCM and the combined organic extracts dried (Na2SO4) filtered and concentrated in vacuo to give 2,4,6-trichloro-5-hydroxy-pyrimidine as a pale tan solid (2.55 g, 71%). 13C NMR (DMSO-d6): 149.23 (C), 145.25 (C), 145.08 (C). LCMS: RT=2.65/2.77 [M−H]−=197/199.

Aufarbeitung

  1. customreaction
  2. temperatureThe reaction mixture was cooled
  3. washThe aqueous layer was washed with DCM
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e20c18e7ce4341dbb38a5e6c4cd57322
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883799B2

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