Phosphorus tribromide → 4-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

HRID 250224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250224
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17]O)[CH2:3][CH2:2]1.P(Br)(Br)[Br:20]>ClCCl>[Br:20][CH2:17][C:5]1[C:6]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

Produkt 1

HCID 593693284-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. solution of (5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-yl)-methanol (0.124 g, 0.44 mmol) in dichloromethane (4 mL) is added phosphorous tribromide (0.261 g, 0.963 mmol). The ice bath is removed after 20 minutes and the reaction is allowed to stir for an additional twenty minutes at room temperature. The reaction mixture is quenched with pH 7 buffer and extracted with dichloromethane several times. The organic layers are combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (0.124 g, 82%). 1H-NMR (400 MHz CDCl3) δ 7.45-7.33 (m, 3H), 4.20 (s, 2H), 2.09 (m, 1H), 1.27 (m, 2H), 1.16 (m, 2H).

Aufarbeitung

  1. customThe ice bath is removed after 20 minutes
  2. customThe reaction mixture is quenched with pH 7 buffer
  3. extractionextracted with dichloromethane several times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ff1af34c827548379c1e097f1263d409
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

Notizen zur Reaktion

Wird geladen…