Trimethyl orthoformate → 1-Bromo-4-(dimethoxymethyl)benzene

HRID 380224

Reaktionsgleichung

Reaktionsgleichung von HRID 380224
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>CO>[CH3:12][O:11][CH:10]([O:13][CH3:14])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 9005Trimethyl orthoformateHCID 707414-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 10942334Sodium Methoxide

Produkt 1

HCID 6883421-Bromo-4-(dimethoxymethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

21.1 g (114 mmol) of 4-bromobenzaldehyde and 20 ml (182 mmol) of trimethyl orthoformate (both Fluka, Buchs, Switzerland) are dissolved in 35 ml of methanol, and 0.65 g (3.4 mmol) of p-toluenesulfonic acid monohydrate is added at room temperature (exothermic reaction). The reaction mixture is stirred at room temperature under nitrogen for 20 hours. The acid is then neutralised with 0.62 ml of 30% sodium methanolate solution in methanol (3.4 mmol); the reaction mixture is concentrated using a rotary evaporator and the residue is distilled. The title compound is obtained in the form of a colourless liquid. TLC: Rf=0.58 (hexane/ethyl acetate 2:1). B.p.: 90-92° C. (4 mbar). 1H-NMR (CDCl3; 200 MHz): 7.50 and 7.32/each d, J=9 (2×2H); 5.36/s (1H); 3.31/s (6H).

Aufarbeitung

  1. custom(exothermic reaction)
  2. concentrationthe reaction mixture is concentrated
  3. customa rotary evaporator
  4. distillationthe residue is distilled

Quellen und Nachweise

ORD-Eintrag
ord-e2989b6615fc46b98d02ee850918d80b
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300519B1

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