Chloromethyl Methyl Ether → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 521746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521746
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][CH2:19]Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:17][O:18][CH3:19]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 134938392-Bromo-5-methoxyphenol

Produkt 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzeneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Protected haloorganoboronic acid 14 was synthesized by a multi-step process. To a stirred mixture of 2-bromo-5-methoxyphenol (Albert, 2002) (2.19 g, 10.8 mmol) and K2CO3 (4.46 g, 32.3 mmol) in acetone (55 mL) was added chloromethyl methyl ether (1.63 mL, 21.5 mmol). The mixture was refluxed for 3 h and then allowed to cool to 23° C. The mixture was filtered and the filtrate was concentrated in vacuo. The crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5) to provide 2-bromo-5-methoxy-1-methoxymethoxybenzene as a colorless liquid (2.43 g, 92%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-7aec9d8df3b547e6b1f7ce28ff5658ed
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328127B2

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