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

HRID 528435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528435
[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 (6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at RT 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 extracted with DCM and the combined organic extracts dried (Na2SO4) 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 (Method C): RT=2.65/2.77. [M−H]+ 197/199.

Aufarbeitung

  1. temperaturewas cooled
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e5dc69e7a60a4ccd8f8a15ccb2fe835c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346817B2

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