StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → 5-Bromo-4-chloro-2-methoxymethoxybenzyl cyanide

HRID 862072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 862072
[Br:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7]O.[CH2:15]([N:17](CC)CC)C.CS(Cl)(=O)=O.O>ClCCl>[Br:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7][C:15]#[N:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 106128525-Bromo-4-chloro-2-methoxymethoxybenzyl alcohol

Produkt 1

HCID 107559665-Bromo-4-chloro-2-methoxymethoxybenzyl cyanide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 5-bromo-4-chloro-2-methoxymethoxybenzyl alcohol (137.9 g) and triethylamine (105 ml) in dichloromethane (500 ml) was added at 0° C. methanesulfonyl chloride (45.5 ml) over a period of 30 minutes. The mixture was stirred overnight (13 hours), while warming up to room temperature. The reaction mixture was poured into water, to which was added dichloromethane for extraction. The extract solution was dried (anhydrous magnesium sulfate) and concentrated. To a suspension of the concentrate and sodium cyanide (51.4 g) in dichloromethane (40 ml) was added dropwise at 0° C. DMSO (300 ml). The mixture was then stirred for 3 hours at room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried (anhydrous magnesium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-4-chloro-2-methoxymethoxybenzyl cyanide (86.4 g) (Compound B-35). The physical properties are shown in [Table 6].

Aufarbeitung

  1. extractionfor extraction
  2. dry with materialThe extract solution was dried (anhydrous magnesium sulfate)
  3. concentrationconcentrated
  4. additionTo a suspension of the
  5. concentrationconcentrate
  6. additionsodium cyanide (51.4 g) in dichloromethane (40 ml) was added dropwise at 0° C
  7. stirringThe mixture was then stirred for 3 hours at room temperature
  8. additionThe reaction mixture was poured into water, which
  9. extractionwas subjected to extraction with ethyl acetate
  10. washThe extract solution was washed with water
  11. dry with materialdried (anhydrous magnesium sulfate)
  12. concentrationconcentrated
  13. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7d98c758b67442c79ad3cadb8fb5f9d7
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05716971

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion