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

HRID 1771685ノート

反応式

HRID 1771685 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 46311127Methyl 2,6-difluoro-3-hydroxybenzoate収率 75%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1b9d1e6ae8aa44158cb5c5c742401b9b
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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