Hydrochloric Acid → HCID 86594064, compound

HRID 1823259Notes

Reaction equation

HRID 1823259 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+].[CH3:14][O:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[C:17]=1Br.Cl>[Cu]Br.O1CCOCC1>[F:22][C:20]1[CH:19]=[C:18]([F:23])[C:17]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[C:16]([O:15][CH3:14])[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 22172577HCID 22172577, compound

Product 1

HCID 86594064HCID 86594064, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °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 60° C. within 2 hours. The mixture was stirred for 10 minutes at 60° C. and copper (I) bromide (0.05 mol) was added. After 15 minutes, a mixture of 2-methoxy-4,6-difluorobromobenzene (0.25 mol) and 1,4-dioxane (10 ml) was added. The reaction mixture was stirred at about 100° C. for about 15 hours. After cooling to about 15 to 20° C. 35 ml of 12N hydrochloric acid were added. The precipitate was filtered off. The filtrate was extracted with diethyl ether. The organic phase was separated, dried and filtered. The filtrate was evaporated to yield 44 g of the title compound.

Workup

  1. waitAfter 15 minutes
  2. additionwas added
  3. stirringThe reaction mixture was stirred at about 100° C. for about 15 hours
  4. temperatureAfter cooling to about 15 to 20° C
  5. filtrationThe precipitate was filtered off
  6. extractionThe filtrate was extracted with diethyl ether
  7. customThe organic phase was separated
  8. customdried
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9ca3d1e692f74b87b003965e2c73838b
Source dataset
uspto-grants-2006_05
Patent number
US07038047B2

Reaction notes

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