Isobutyric Acid → 5-Bromo-5-chloro-4-(1,1-dimethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene

HRID 1379303Notes

Reaction equation

HRID 1379303 reaction equation
[Br:1][C:2]([Cl:13])([C:9]([F:12])([F:11])[F:10])[CH:3]([OH:8])[CH:4]=[C:5]([CH3:7])[CH3:6].[C:14](OC)([O:18][CH3:19])([O:16][CH3:17])[CH3:15].C(O)(=O)C(C)C>>[Br:1][C:2]([Cl:13])([C:9]([F:10])([F:11])[F:12])[CH:3]([O:8][C:14]([O:18][CH3:19])([O:16][CH3:17])[CH3:15])[CH:4]=[C:5]([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 6590Isobutyric AcidHCID 15050Trimethyl orthoacetateHCID 152193461,1,1-Trifluoro-2-bromo-2-chloro-5-methyl-4-hexen-3-ol

Product 1

HCID 152787025-Bromo-5-chloro-4-(1,1-dimethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene

Conditions

Temperature
111 °C

Procedure

5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (48.0 g) and isobutyric acid (0.29 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and Dean and Stark received packed with 5 A molecular seives. The mixture was heated with agitation to reflux and distillates collected until reaction mass temperature increased to 111° C. (ca. 1 hr). Once the reaction was complete, the residual trimethyl orthoacetate was removed by distillation under vacuum (ca. 50° C. @50 mmHg) to give the product, 5-bromo-5-chloro-4-(1,1-dimethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene, as an orange oil (10.9 g, 85% yield).

Workup

  1. customfitted with: nitrogen inlet/bubbler
  2. temperatureThe mixture was heated with agitation
  3. temperatureto reflux
  4. distillationdistillates collected until reaction mass temperature
  5. customthe residual trimethyl orthoacetate was removed by distillation under vacuum (ca. 50° C. @50 mmHg)

Sources & evidence

ORD record
ord-745123934fba45c1b69853c803b3fa59
Source dataset
uspto-grants-1997_09
Patent number
US05670697

Reaction notes

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