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Trimethyl orthoformate → 2-Bromo-1-[3-(pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanone

HRID 1258537
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Reaktionsgleichung

Reaktionsgleichung von HRID 1258537
[F:1][S:2]([F:20])([F:19])([F:18])([F:17])[C:3]1[CH:4]=[C:5]([C:14](=[O:16])[CH3:15])[CH:6]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=1.C(OC)(OC)OC.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O.[Br-:43].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>CO.C1COCC1>[Br:43][CH2:15][C:14]([C:5]1[CH:6]=[C:7]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:8]=[C:3]([S:2]([F:1])([F:17])([F:18])([F:19])[F:20])[CH:4]=1)=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 65617D-Camphorsulfonic AcidHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581374371-[3-(Pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanone

Produkt 1

HCID 581374592-Bromo-1-[3-(pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanoneAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-[3-(Pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanone (78 mg) was dissolved in methanol (5 ml) and admixed while stirring with trimethyl orthoformate (80 mg) and DL-10-camphorsulfonic acid (57 mg). After stirring at RT for 3 h, THF (5 ml) was added, followed by phenyltrimethylammonium tribromide (83 mg). After stirring at RT for 3 h, the mixture was left to stand overnight. Then the mixture was heated to 50° C. for 3 h and subsequently dried. The residue was taken up in ACN, admixed with 2N sulfuric acid and stirred for 30 min. Then it was admixed with water and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, admixed with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 9 mg of the desired compound were obtained.

Aufarbeitung

  1. stirringAfter stirring at RT for 3 h
  2. waitthe mixture was left
  3. waitto stand overnight
  4. temperatureThen the mixture was heated to 50° C. for 3 h
  5. customsubsequently dried
  6. stirringstirred for 30 min
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC
  9. extractionextracted three times with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4ee706fd6cfd42d58188d4ef8a0b80c0
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466169B2

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