Hydrochloric Acid → Diethyl (2-fluoro-4-methylphenyl)malonate

HRID 10758

Reaction equation

HRID 10758 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[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[F:22].Cl>O1CCOCC1>[F:22][C:16]1[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 17974023Diethyl (2-fluoro-4-methylphenyl)malonateYield 59.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

0.49 mol of diethyl malonate was added at 60° C. inside 2 hours to a mixture of 0.51 mol of NaH and 140 ml of 1,4-dioxane. The mixture was stirred for approximately 10 min at 60° C. and then 0.05 mol of Cu(I)Br was added. After 15 min, a mixture of 0.25 mol of 4-bromo-3-fluorotoluene and 10 ml of 1,4-dioxane was added. The reaction mixture was heated at 100° C. for approximately 15 hours and was then cooled to 15° C. After acidifying with 35 ml of 12N HCl at 15 to 20° C., the precipitate produced was filtered off. The filtrate was extracted and the organic phases, after separation, were dried and then freed from the solvent. 40 g of the title compound were obtained.

Workup

  1. waitAfter 15 min
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 100° C. for approximately 15 hours
  4. temperaturewas then cooled to 15° C
  5. customthe precipitate produced
  6. filtrationwas filtered off
  7. extractionThe filtrate was extracted
  8. customthe organic phases, after separation
  9. customwere dried

Sources & evidence

ORD record
ord-040a36dbcef644d3b7a53d23ebd88f75
Source dataset
uspto-grants-2006_08
Patent number
US07094894B2

Linked notes

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