Bromine → HCID 86682804, Verbindung

HRID 1504328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504328
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH2:13][OH:14].[Br:15]Br>S(=O)(=O)(O)O.O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:15][C:6]1[C:5]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:4][C:3]([CH2:13][OH:14])=[C:2]([Cl:1])[CH:7]=1

Komponenten

6

Edukt 2

HCID 24408BromineHCID 717442072-Chloro-5-trifluoromethoxybenzyl alcohol

Produkt 1

HCID 86682804HCID 86682804, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418844HCID 178418844, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-5-trifluoromethoxy-phenyl)-methanol (16.3 g, 71.94 mmol) in sulfuric acid (200 mL) and water (60 mL) was added bromine (12.65 g, 79.13 mmol), followed by silver sulfate (12.34 g, 39.57 mmol). The reaction mixture was stirred at RT for 1 h, poured onto ice, and then extracted with EtOAc (3×100 mL). The organic layers were combined, dried over Na2SO4 and concentrated to afford crude product, which was purified by flash chromatography (0-10% EtOAc in petroleum ether) to give the title intermediate (6.0 g, 27% yield). (m/z): [M−OH]+ calcd for C8H5BrClF3O2 286.91; 288.91. found 289.0.

Aufarbeitung

  1. additionpoured onto ice
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto afford crude product, which
  6. customwas purified by flash chromatography (0-10% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-9c0f8639466e4538bba5d763f3fbf189
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212168B2

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