Boron tribromide → HCID 11595444, Verbindung

HRID 1817500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817500
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:24][CH2:25][CH3:26])[N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:24][CH2:25][CH3:26])[N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 69058159HCID 69058159, Verbindung

Produkt 1

HCID 11595444HCID 11595444, VerbindungAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3-methoxyphenyl)[1-propyl-7-(trifluoromethyl)-1H-indazol-3-yl]methanone (0.24 g, 0.66 mmol) in 10 mL of CH2Cl2 containing 0.2 mL cyclohexene was cooled to −78° C. under an argon atmosphere. Boron tribromide (0.25 mL, 2.65 mmol) was added in one portion and the reaction mixture was allowed to warm to ambient temperature. The reaction was quenched by the careful addition of methanol. The reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The solvents were removed in vacuo and the residue purified by flash chromatography to give 0.077 g of the title compound (mp 118° C.) as a light yellow solid.

Aufarbeitung

  1. customThe reaction was quenched by the careful addition of methanol
  2. customThe reaction mixture was partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed in vacuo
  6. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d2cc5fb8756648ddbc66936b8abeac43
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598286B2

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