Carbon Dioxide → HCID 18791030, compound

HRID 1005290Notes

Reaction equation

HRID 1005290 reaction equation
C([Mg]Cl)(C)C.[CH2:6]([O:9][C:10]1[CH:15]=[C:14](Br)[C:13]([F:17])=[CH:12][C:11]=1[Cl:18])[CH:7]=[CH2:8].[C:19](=[O:21])=[O:20].Cl>O1CCCC1>[CH2:6]([O:9][C:10]1[C:11]([Cl:18])=[CH:12][C:13]([F:17])=[C:14]([CH:15]=1)[C:19]([OH:21])=[O:20])[CH:7]=[CH2:8]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 18791037HCID 18791037, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 18791030HCID 18791030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 20-25 C., 200 ml (0.4 mol) of a 2 M solution of isopropyl-magnesium chloride and tetrahydrofuran were added over a period of 30 minutes to a solution of 85 g (0.32 mol) of 1-allyloxy-5-bromo-2-chloro-4-fluorobenzene in 200 ml of tetrahydrofuran. The mixture was then stirred for 30 minutes and 50 g (1.1 mol) of dry ice were added with ice-cooling. The mixture was subsequently stirred for 16 hours, after which 250 ml of a 10% strength hydrochloric acid were added with ice-cooling. The aqueous phase was separated off and extracted with methyl tert-butyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. The crude product was purified by trituration with a little n-hexane and the precipitated product of value was filtered off. Yield: 59.7 g.

Workup

  1. temperaturecooling
  2. stirringThe mixture was subsequently stirred for 16 hours
  3. temperaturecooling
  4. customThe aqueous phase was separated off
  5. extractionextracted with methyl tert-butyl ether
  6. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationfinally concentrated
  9. customThe crude product was purified by trituration with a little n-hexane
  10. filtrationthe precipitated product of value was filtered off

Sources & evidence

ORD record
ord-a1b52f4a914b4097804da5202b7c412d
Source dataset
uspto-grants-2000_04
Patent number
US06054413

Reaction notes

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