Dimethylformamide → 1-Bromo-2-(chloromethyl)-3-fluorobenzene

HRID 889144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889144
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9]O.CN(C)C=O.[OH-].[Na+].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][Cl:20]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 44181801(2-Bromo-6-fluorophenyl)methanol

Produkt 1

HCID 547587241-Bromo-2-(chloromethyl)-3-fluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

After dissolving (2-bromo-6-fluorophenyl)methanol (CAS 261723-33-5) (4.07 g) in toluene (50 ml), thionyl chloride (2.21 ml) was added dropwise while stirring on ice. N,N-Dimethylformamide (0.1 ml) was then added and the mixture was stirred for 6 hours. The reaction mixture was diluted with water, a 1N aqueous solution of sodium hydroxide was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain the title compound (4.45 g).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for 6 hours
  3. extractionextraction
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4b66c80d7b7b4579a674d034a7875193
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252810B2

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