Dimethyl Sulfate → 1-Chloro-3-fluoro-2-(methoxymethyl)benzene

HRID 266589

Reaktionsgleichung

Reaktionsgleichung von HRID 266589
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5].[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>ClCCl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][O:5][CH3:17]

Komponenten

7

Edukt 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 918682-Chloro-6-fluorobenzyl alcohol

Produkt 1

HCID 537737161-Chloro-3-fluoro-2-(methoxymethyl)benzeneAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Chloro-6-fluorobenzyl alcohol (50 g) was stirred in dichloromethane and a solution of sodium hydroxide (32 g) in water was added. After 30 minutes stirring the mixture was cooled to 0° C. when dimethyl sulphate (47 g) and tetrabutyl-ammonium hydrogen-sulphate (1 g) were added dropwise. The mixture was allowed to warm to room temperature and stirred for 3 hours. It was quenched with water and extracted with dichloromethane. The organic extract was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue distilled under reduced pressure yielding 1-chloro-3-fluoro-2-methoxymethylbenzene (27.3 g) b.p. 82°-95° C./24 mm Hg.

Aufarbeitung

  1. additionwere added dropwise
  2. stirringstirred for 3 hours
  3. customIt was quenched with water
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. distillationthe residue distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e42036ea766a4b53b9c8307ff400b3a9
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650533

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