HCID 58938153, compound → Benzoic acid, 3-fluoro-5-methyl-, methyl ester

HRID 273093Notes

Reaction equation

HRID 273093 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[C:6]([F:12])[CH:5]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([F:12])[CH:5]=1

Participants

4

Reactant 1

HCID 58938153HCID 58938153, compound

Product 1

HCID 44203100Benzoic acid, 3-fluoro-5-methyl-, methyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethanol (2 ml) was added to round bottom flask containing 3-fluoro-5-hydroxymethyl-benzoic acid methyl ester (667 mg, 3.6 mmol) and palladium (10 wt. % on activated carbon, 300 mg) under argon. The flask was evacuated using a water aspirator and then filled with hydrogen from a balloon. After stirring for 2 h, the palladium on carbon was removed by filtration through celite. The filtrate was then concentrated to afford 520 mg (87%) of 3-fluoro-5-methyl-benzoic acid methyl ester. 1H NMR (CDCl3), δ (ppm): 7.65 (s, 1H), 7.51 (d, 1H), 7.08 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen from a balloon
  3. customthe palladium on carbon was removed by filtration through celite
  4. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-a5bb3d3a018a431f9047483cc65801ce
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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