Potassium hydroxy sulfite → 4-Fluoro-3-(methoxycarbonyl)benzoic acid

HRID 551980Notes

Reaction equation

HRID 551980 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:5]=1[F:12].[OH:14]OS([O-])=O.[K+]>CN(C=O)C>[F:12][C:5]1[CH:6]=[CH:7][C:8]([C:10]([OH:14])=[O:11])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 24971957Methyl 2-fluoro-5-formylbenzoate

Product 1

HCID 575544904-Fluoro-3-(methoxycarbonyl)benzoic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl-2-fluoro-5-formylbenzoate (2 g, 0.0109 mol) in dry DMF (75 mL) was added oxone (Aldrich, 6.75 g, 0.0109 mol) and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was then quenched with 1.5M.HCl (50 mL) and the product was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, brine, dried over magnesium sulfate filtrated and concentrated to give 1.7 g (78%) of the titled compound as a solid. TLC: Chloroform/methanol (9/1), Rf=0.2, HPLC purity >99%. 1H NMR (DMSO) δ: 8.44 (m, 1H), 8.19 (m, 1H), 7.48 (m 1H), 3.88 (s, 1H).

Workup

  1. customThe reaction mixture was then quenched with 1.5M
  2. extractionHCl (50 mL) and the product was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44c9097765c848babfa520f7a6262685
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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