Hydrochloric Acid → Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

HRID 1581553Notes

Reaction equation

HRID 1581553 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=1[F:23].Cl>[Cu]Br.O1CCOCC1>[F:21][C:20]1[CH:15]=[C:16]([F:23])[CH:17]=[C:18]([F:22])[C:19]=1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl Malonate2×HCID 24758Sodium hydrideHCID 753981-Bromo-2,4,6-trifluorobenzene

Product 1

HCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
55 °C

Procedure

Diethyl malonate (0.49 mol) was added to a mixture of sodium hydride (0.51 mol) and 1,4-dioxane (140 ml) at 55 to 60° C. within 2 hours. A mixture of 1,4-dioxane (50 ml) and diethyl malonate (0.13 mol) was added. The mixture was stirred for 10 minutes at 55° C. and copper(I) bromide (0.05 mol) was added. After 15 min. a mixture of 2-bromo-1,3,5-trifluorobenzene (0.25 mol) and 1,4-dioxane (10 ml) was added. The reaction mixture was heated at 100° C. for 15 hours and cooled to 15° C. Hydrochloric acid (12N, 35 ml) was added slowly at 15 to 20° C. The precipitate was filtered off. The filtrate was extracted with diethylether. The organic Phase was separated, dried with anhydrous sodium sulphate and filtered. The filtrate was evaporated under reduced Pressure to yield the product.

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 100° C. for 15 hours
  4. temperaturecooled to 15° C
  5. filtrationThe precipitate was filtered off
  6. extractionThe filtrate was extracted with diethylether
  7. customThe organic Phase was separated
  8. dry with materialdried with anhydrous sodium sulphate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced Pressure
  11. customto yield the product

Sources & evidence

ORD record
ord-a81ef9b6ed624d92a97063a28b6fea60
Source dataset
uspto-grants-2004_05
Patent number
US06730680B2

Reaction notes

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