Tetrahydrofuran → 1-Bromo-4-fluoro-2,5-bis[(1-methoxy-1-methylethoxy)methyl]benzene

HRID 221919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221919
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][OH:12].[CH3:13][O:14][C:15]([CH3:17])=[CH2:16].[C:18](=[O:21])([O-])O.[Na+].O1C[CH2:26][CH2:25][CH2:24]1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:15]([CH3:17])([O:14][CH3:13])[CH3:16])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][O:12][C:25]([O:21][CH3:18])([CH3:26])[CH3:24]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 59278999(2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol

Produkt 1

HCID 594887661-Bromo-4-fluoro-2,5-bis[(1-methoxy-1-methylethoxy)methyl]benzeneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6101p-Toluenesulfonic acidKatalysator

Versuchsvorschrift

(2-Bromo-5-fluoro-4-hydroxymethylphenyl)-methanol (71.3 mg, 0.303 mmol) was dissolved in tetrahydrofuran (1 mL), and 2-methoxypropene (214.7 mg, 2.97 mmol) was added thereto. The resultant mixture was cooled to 0° C., and then p-toluenesulfonic acid (1.0 mg. 0.0029 mmol) was added thereto. This mixture was stirred for 40 minutes, and then saturated aqueous sodium hydrogen carbonate was added. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (111.7 mg, 97%).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c6bb24346a804e0f93bba34cd9f536cb
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207134B2

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