Carbon Dioxide → 3-Bromo-5-fluorobenzoic acid

HRID 1356826Notes

Reaction equation

HRID 1356826 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([Br:12])[CH:6]=1.[C:13](=[O:15])=[O:14].Cl>CCOCC.O>[Br:12][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([F:11])[CH:8]=1)[C:13]([OH:15])=[O:14]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 807IodineHCID 1370031,3-Dibromo-5-fluorobenzeneHCID 5462224Magnesium

Product 1

HCID 27733393-Bromo-5-fluorobenzoic acidYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Magnesium turnings (1.97 g) and iodine (catalytic amount) were added to ether (150 ml), and 1,3-dibromo-5-fluorobenzene (19.6 g) in ether (20 ml) was added dropwise under nitrogen atmosphere at such a rate that gentle reflux occurred. The mixture was refluxed for 3 hours, and left to cool. Crushed dry ice was added thereto, and the mixture was stirred for 1 hour. The reaction mixture was poured into water, and acidified with hydrochloric acid. The mixture was extracted with ether (200 ml), and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1), to thereby yield 9.37 g of the target compound (yield: 55.4%).

Workup

  1. additionwas added dropwise under nitrogen atmosphere at such a rate
  2. temperaturethat gentle reflux
  3. temperatureThe mixture was refluxed for 3 hours
  4. waitleft
  5. temperatureto cool
  6. extractionThe mixture was extracted with ether (200 ml)
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-6775ff910faa4f119f70b65e6030ead4
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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