Water → HCID 22731282, Verbindung

HRID 2085577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085577
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.Cl[CH:14]([O:16]C(Cl)Cl)Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[O:16])[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 558102Bis(dichloromethyl) etherHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran2×

Produkt 1

HCID 22731282HCID 22731282, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred, cooled (ice-bath) solution of 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran (Intermediate 2, 0.4 g, 1.57 mmol) in anhydrous dichloromethane(4 mL), titanium tetrachloride (0.172 mL, 1.57 mmol) was added followed by dichloromethyl ether (0.14 mL, 1.57 mmol). The reaction mixture was allowed to warm to room temperature and at the end of 3 hr, the reaction mixture was poured into iced water and extracted with diethyl ether. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to a residue that on flash column chromatography using 2.5% ethyl acetate in hexane as the eluent afforded the title compound (0.25 g, 63%).

Aufarbeitung

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a residue that on flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-65f55275dbab412a88bdae2e5d49c9df
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720423B2

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