Carbon Dioxide → Benzoic acid, 2-chloro-4-fluoro-5-methyl-

HRID 369241Notes

Reaction equation

HRID 369241 reaction equation
C([Li])CCC.Br[C:7]1[C:8]([Cl:15])=[CH:9][C:10]([F:14])=[C:11]([CH3:13])[CH:12]=1.[C:16](=[O:18])=[O:17].O>C(OCC)C>[Cl:15][C:8]1[CH:9]=[C:10]([F:14])[C:11]([CH3:13])=[CH:12][C:7]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 27732735-Bromo-4-chloro-2-fluorotolueneHCID 178418339Butyllithium

Product 1

HCID 23284674Benzoic acid, 2-chloro-4-fluoro-5-methyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (1.69 M hexane solution; 14 ml) was added dropwise to a solution of 5-bromo-4-chloro-2-fluorotoluene (5.6 g) in absolute diethyl ether (100 ml) at -70° C. in a nitrogen gas stream, and the mixture was stirred at the same temperature for 1 hour. Carbon dioxide was blown into the mixture at -70° C. for 30 minutes. The temperature of the reaction mixture was given back to room temperature to conduct stirring for 2 days. Diethyl ether and water were added to the reaction mixture to conduct liquid separation. A water layer was collected, to which concentrated hydrochloric acid was added to acidify the water layer. The water layer was then Extracted with diethyl ether. An organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain the title compound (3.3 g) as a yellow solid.

Workup

  1. customwas given back to room temperature
  2. stirringto conduct stirring for 2 days
  3. customliquid separation
  4. customA water layer was collected, to which concentrated hydrochloric acid
  5. additionwas added
  6. extractionThe water layer was then Extracted with diethyl ether
  7. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-768cd209d1444287b67d9f2af447519f
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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