Trimethyl orthoformate → 1-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene

HRID 1258535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258535
[Br:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:7]=1.CC1(C)[C@]2(CS(O)(=O)=O)[C:23](C[C@H]1CC2)=[O:24].[CH:32](OC)(OC)OC.C(=O)([O-])O.[Na+]>CO.O.CC(=O)OCC>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([F:13])([F:9])([F:10])([F:11])[F:12])[CH:5]=[C:4]([C:14]([O:24][CH3:23])([O:16][CH3:32])[CH3:15])[CH:3]=1

Komponenten

8

Edukt 4

HCID 9005Trimethyl orthoformateHCID 65617D-Camphorsulfonic AcidHCID 516892Sodium BicarbonateHCID 581374301-[3-Bromo-5-(pentafluorosulfanyl)phenyl]ethanone

Produkt 1

HCID 581374181-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-[3-Bromo-5-(pentafluorosulfanyl)phenyl]ethanone (835 mg, example 26c) was dissolved in methanol (50 ml), and admixed at RT with DL-10-camphorsulfonic acid (0.9 mg) and with trimethyl orthoformate (0.85 ml). The reaction mixture was stirred at RT for 2 h and then stood overnight. Then the mixture was stirred at RT for a further 5 h. Subsequently, saturated sodium hydrogencarbonate solution was used to adjust the pH to 9, and a large amount of EA and water were added. The organic phase was removed and the aqueous phase was extracted five times with EA. The combined EA phases were dried over magnesium sulfate, filtered and concentrated. 900 mg of the title compound were obtained.

Aufarbeitung

  1. waitstood overnight
  2. stirringThen the mixture was stirred at RT for a further 5 h
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was extracted five times with EA
  5. dry with materialThe combined EA phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67a3fe0be9d54674a2dd31830bd7b68b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466169B2

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