Methanol → Methyl 2,6-difluoro-3-hydroxybenzoate

HRID 1771685Notes

Reaction equation

HRID 1771685 reaction equation
[F:1][C:2]1[C:10]([O:11][Si](C(C)C)(C(C)C)C(C)C)=[CH:9][CH:8]=[C:7]([F:22])[C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:27]O>>[F:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]([F:22])[C:3]=1[C:4]([O:6][CH3:27])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 894436202,6-Difluoro-3-triisopropylsilyloxy-benzoic acid

Product 1

HCID 46311127Methyl 2,6-difluoro-3-hydroxybenzoateYield 75%

Procedure

To a solution of 2,6-difluoro-3-triisopropylsilyloxy-benzoic acid (see example 2) (7 g, 21.1 mmol, 1.0 eq) in MeOH (100 mL) was added SOCl2 (10 mL) dropwise. The reaction mixture was heated at reflux for 3 h, then cooled and the solvent removed in vacuo. Water was added and the aqueous layer was extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a solid (3 g, 75%) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. additionWater was added
  6. extractionthe aqueous layer was extracted with EtOAc
  7. extractionThe organic extract
  8. washwas washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b9d1e6ae8aa44158cb5c5c742401b9b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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