Carbon Dioxide → 2-Fluoro-4-(trifluoromethoxy)benzoic acid

HRID 1407195Notes

Reaction equation

HRID 1407195 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[F:13].C([Mg]Br)(C)C.[C:19](=[O:21])=[O:20]>C1COCC1>[F:13][C:3]1[CH:4]=[C:5]([O:8][C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][C:2]=1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 220652111-Bromo-2-fluoro-4-(trifluoromethoxy)benzeneHCID 178418365HCID 178418365, compound

Product 1

HCID 580723032-Fluoro-4-(trifluoromethoxy)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (8 g, 30.8 mmol) in 170 mL of THF was cooled to −40° C., and then i-PrMgBr (0.4 mol/L in THF, 91 mL) was injected. After being stirred for 3 h, CO2 was injected for 2 h at 0° C. The mixture was washed with 1M HCl aqueous solution, separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, and concentrated under reduced pressure. The residue was washed with petroether to give the title compound (6 g, 87% yield): 1H NMR (400 MHz, CDCl3): δ ppm 7.05-7.12 (m, 2H), 8.10 (t, J=8.4 Hz, 1H).

Workup

  1. washThe mixture was washed with 1M HCl aqueous solution
  2. customseparated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with petroether

Sources & evidence

ORD record
ord-1cf2bd71bc304bb5ac69144daa88080a
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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