Oxalyl chloride → Methyl 4-fluoro-2-methylbenzoate

HRID 2427490Notes

Reaction equation

HRID 2427490 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[C:12](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[CH3:11]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 2782181Methyl 4-fluoro-2-methylbenzoateYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-2-methylbenzoic acid (1.6 g, 10.3 mmol) was dissolved in CH2Cl2 (20 mL) and DMF (1 drop) and stirred as oxalyl chloride (10.3 mL, 20.8 mmol) was added. The reaction stirred for 15 minutes before the solvent was removed under reduced pressure. The product was dissolved in anhydrous CH2Cl2 and MeOH (5 mL) and stirred for a further 15 minutes. The solvent was removed under reduced pressure and purified by column chromatography on silica (2% EtOAc/Hexanes) to afford a colourless oil (1.33 g). 1H NMR (300 MHz, CDCl3): δ 7.95 (d, 1H), 6.96 (d, 1H), 6.75-6.77 (m, 1H), 3.86 (d, 3H), 2.62 (d, 3H).

Workup

  1. additionwas added
  2. customwas removed under reduced pressure
  3. dissolutionThe product was dissolved in anhydrous CH2Cl2
  4. stirringMeOH (5 mL) and stirred for a further 15 minutes
  5. customThe solvent was removed under reduced pressure
  6. custompurified by column chromatography on silica (2% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-1114561ff56e48bf9adb5cae616daca3
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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