Diethyl Ether → 3-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde

HRID 1765855

Reaktionsgleichung

Reaktionsgleichung von HRID 1765855
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[CH2:14]([O:16]CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1)[CH:14]=[O:16]

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol2×

Produkt 1

HCID 211071503-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehydeAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred, cooled (ice bath) solution of 4-bromo-2-tert-butyl-5-methyl-phenol (Intermediate 139, 0.85 g, 3.5 mmol) in anhydrous dichloromethane (7 mL) was treated with titanium tetrachloride (0.64 mL, 5.8 mmol) followed by α,α-dichloro methyl ether (0.3 g, 3.5 mmol). The reaction mixture was allowed to warm to ambient temperature for 4 h. The reaction mixture was diluted with diethyl ether, washed with brine (×1) and dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230–400 mesh) using 1% ethyl acetate in hexane to afford the title compound as a yellow solid (0.58 g, 61%).

Aufarbeitung

  1. washwashed with brine (×1)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a residue which

Quellen und Nachweise

ORD-Eintrag
ord-4d4f1513ee864168b68e8f9d309f3b12
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226951B2

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