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Triethylamine → 1-Bromo-4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}benzene

HRID 511720
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511720
[F:1][C:2]([F:8])(F)S([O-])(=O)=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13](C2SCCC[S+]=2)=[CH:12][CH:11]=1.[F:22][C:23]([F:36])([F:35])[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.C(N(CC)CC)C.F.F.F.C(N(CC)CC)C.BrBr>ClCCl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]([F:8])([F:1])[O:34][C:31]2[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][CH2:24][C:23]([F:35])([F:36])[F:22])=[CH:29][CH:30]=2)=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 24408BromineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 674549644-(4,4,4-Trifluorobutoxy)phenolHCID 866765562-(4-bromophenyl)-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonate

Produkt 1

HCID 86676557
1-Bromo-4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}benzene
Ausbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-55 °C

Versuchsvorschrift

69.3 g (164 mmol) of 2-(4-bromophenyl)-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonate, are solubilised in 750 mL of dichloromethane. The solution is cooled down to −55° C. 53.94 g (245 mmol) of 4-(4,4,4-trifluorobutoxy)phenol and 36.5 ml (262 mmol) of triethylamine dissolved in 300 ml of dichloromethane is added to the previous solution. The solution was cooled down to −70° C. and stirred for 45 minutes. 120 ml (736 mmol) of triethylamine trihydrofluoride are added to the mixture. A solution of 8.43 ml (164 mmol) of bromine in 60 ml of dichloromethane is added at this temperature. The reaction is stirred for one hour. The reaction is quenched by addition of NaHCO3. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Chromatography of the residue on 400 g silica gel using toluene: ethyl acetate 95:5 as eluent yields 42 g of 1-bromo-4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}benzene.

Aufarbeitung

  1. additionis added to the previous solution
  2. temperatureThe solution was cooled down to −70° C.
  3. stirringThe reaction is stirred for one hour
  4. customThe reaction is quenched by addition of NaHCO3
  5. washThe organic phase is washed repeatedly with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83684ea9a74e4a04be52b400ea666508
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09097938B2

Notizen zur Reaktion

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