Bromine → 5-Bromo-1,3-difluoro-2-(methylsulfanyl)benzene

HRID 732809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732809
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9][CH3:10].[Br:11]Br.[Cl-].[Al+3].[Cl-].[Cl-].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].C(OCC)C.ClCCl>[Br:11][C:6]1[CH:7]=[C:2]([F:1])[C:3]([S:9][CH3:10])=[C:4]([F:8])[CH:5]=1

Komponenten

8

Edukt 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 6451240Aluminum(III) ChlorideHCID 132502621,3-Difluoro-2-(methylsulfanyl)benzene

Produkt 1

HCID 235966125-Bromo-1,3-difluoro-2-(methylsulfanyl)benzeneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%).

Aufarbeitung

  1. customat 0° C
  2. customSeparate the layers
  3. washwash the organic layer with brine (20 mL)
  4. dry with materialDry with MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. washChromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-26601702e79c46caac2d00bb9b4862b2
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585977B2

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