Trimethyl orthoacetate → Methyl 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate

HRID 3015

Reaktionsgleichung

Reaktionsgleichung von HRID 3015
[Br:1][C:2]([Cl:13])([C:9]([F:12])([F:11])[F:10])[CH:3](O)[CH:4]=[C:5]([CH3:7])[CH3:6].[C:14](OC)([O:18][CH3:19])([O:16]C)[CH3:15]>O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>[Br:1][C:2]([Cl:13])([C:9]([F:10])([F:11])[F:12])[CH:3]=[CH:4][C:5]([CH3:7])([CH3:6])[CH2:15][C:14]([O:18][CH3:19])=[O:16]

Komponenten

4

Edukt 2

HCID 15050Trimethyl orthoacetateHCID 152193461,1,1-Trifluoro-2-bromo-2-chloro-5-methyl-4-hexen-3-ol

Produkt 1

HCID 54451067Methyl 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 71586775BentoniteKatalysator

Reaktionsbedingungen

Temperatur
111 °C

Versuchsvorschrift

5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (16.0 g) and Montmorillonite KSF (0.5 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and still-head. The mixture was heated with agitation, and the methanol-trimethyl orthoacetate distillates were collected until the reactor temperature increased to 111° C. (ca. 1 hr). The reaction was then heated to 135° C. and held for a further 1 hour. The methanol/trimethyl orthoacetate distillates were recharged and the distillation procedure repeated twice. Once the reaction was complete, the Montmorillonite was removed by filtration. The residual trimethyl orthoacetate was then removed by distillation under vacuum (ca. 50° C. @ 100 mmHg) to give the product, methyl 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate as a brown oil (7.8 g, 59% yield).

Aufarbeitung

  1. customfitted with: nitrogen inlet/bubbler
  2. temperatureThe mixture was heated with agitation
  3. distillationthe methanol-trimethyl orthoacetate distillates were collected until the reactor temperature
  4. temperatureThe reaction was then heated to 135° C.
  5. distillationthe distillation procedure
  6. customthe Montmorillonite was removed by filtration
  7. customThe residual trimethyl orthoacetate was then removed by distillation under vacuum (ca. 50° C. @ 100 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-974d91301ba44ad1ab30f6b6ace60cf9
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731475

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