4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol → Tefluthrin

HRID 2182051Notes

Reaction equation

HRID 2182051 reaction equation
[Cl:1]/[C:2](=[CH:7]\[C@@H:8]1[C@H:10]([C:11](Cl)=[O:12])[C:9]1([CH3:15])[CH3:14])/[C:3]([F:6])([F:5])[F:4].[CH3:16][C:17]1[C:24]([F:25])=[C:23]([F:26])[C:20]([CH2:21][OH:22])=[C:19]([F:27])[C:18]=1[F:28]>>[Cl:1]/[C:2](/[C:3]([F:6])([F:5])[F:4])=[CH:7]\[C@@H:8]1[C@H:10]([C:11]([O:22][CH2:21][C:20]2[C:19]([F:27])=[C:18]([F:28])[C:17]([CH3:16])=[C:24]([F:25])[C:23]=2[F:26])=[O:12])[C:9]1([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 27342094-Methyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 11534837TefluthrinYield 104.3%

Conditions

Temperature
80 °C

Procedure

Cis-Z 3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropane carbonyl chloride (257 g) was charged to a reactor fitted with an agitator, thermometer, sub-surface nitrogen inlet and jacketed dropping funnel. Nitrogen sparging was applied to the acid chloride and maintained throughout subsequent processing. Molten 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol (188.1 g) was charged to the dropping funnel. The temperature in the funnel was maintained at 80° C. The alcohol was charged to the acid chloride mixture over three hours. The maximum reaction temperature allowed during the addition was 45° C. On completion of the addition the temperature of the reaction mass was raised to 95° C. and held for 2 hours. GC analysis was used to determine if full conversion of acid chloride had occurred and that no excess reactants were remaining. The mixture was cooled to 60° C. and the molten reaction mass discharged, weighed and analysed. The reaction yielded 423.3 g of molten 4-methyl-2,3,5,6-tetrafluorobenzyl cis-3-((Z)-2-chloro-3,3.3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane carboxylate, analysis against a known standard showed this material to be 92.5 wt % giving an overall reaction yield of 96.5%.

Workup

  1. customfitted with an agitator
  2. customthermometer, sub-surface nitrogen inlet and jacketed dropping
  3. temperaturemaintained throughout subsequent processing
  4. additionThe maximum reaction temperature allowed during the addition
  5. customwas 45° C
  6. additionOn completion of the addition the temperature of the reaction mass
  7. temperaturewas raised to 95° C.
  8. temperatureThe mixture was cooled to 60° C.

Sources & evidence

ORD record
ord-785616fbcbcb435bac98f804d4cb2230
Source dataset
uspto-grants-2005_05
Patent number
US06894195B2

Reaction notes

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