Carbon Dioxide → 4-Chloro-3-fluorobenzoic acid

HRID 1492393Notes

Reaction equation

HRID 1492393 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([F:14])[CH:8]=1.[C:15](=[O:17])=[O:16].O>CCOCC>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:15]([OH:17])=[O:16])=[CH:8][C:9]=1[F:14]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 27246904-Bromo-1-chloro-2-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 27365364-Chloro-3-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (2.5M in hexanes, 176 ml) was added to a stirred solution of 1-bromo-4-chloro-3-fluorobenzene (83.38 g) in dry ether. Stirring was maintained for a further 2.5 hours at -78° C., and the mixture poured onto excess solid carbon dioxide pellets, allowed to reach room temperature and water added. The mixture was washed with ether, acidified, extracted (ethyl acetate) and dried (magnesium sulphate). After evaporation the residue was triturated with petroleum ether to give 4-chloro-3-fluorobenzoic acid (66.4 g) as a white solid, m.p. 192°-192.5° C.

Workup

  1. customto reach room temperature
  2. washThe mixture was washed with ether
  3. extractionextracted (ethyl acetate)
  4. dry with materialdried (magnesium sulphate)
  5. customAfter evaporation the residue
  6. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-a439726447c243b9b46c868c4565543a
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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