Water → (6-Bromo-3-fluoropyridin-2-yl)methanol

HRID 1258556ノート

反応式

HRID 1258556 の反応式
[Br:1][C:2]1[N+:7]([O-])=[C:6]([CH3:9])[C:5]([F:10])=[CH:4][CH:3]=1.C([O-])([O-])=[O:12].[K+].[K+].O>C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>[Br:1][C:2]1[N:7]=[C:6]([CH2:9][OH:12])[C:5]([F:10])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 866531136-Bromo-3-fluoro-2-methylpyridine 1-oxide

生成物 1

HCID 53485567(6-Bromo-3-fluoropyridin-2-yl)methanol収率 87.9%

試薬・触媒・溶媒 1

HCID 9845Trifluoroacetic anhydride溶媒

実験手順

6-bromo-3-fluoro-2-methylpyridine 1-oxide (2.89 g, 14.02 mmol, 1 eq.) was dissolved in neat TFAA (10 ml) and stirred 30 min at room temperature and refluxed for 2 hrs. The solvent was evaporated and the residue diluted with DCM and basified with sat. aqueous Na2CO3. The organic layers was separated and washed with sat. aqueous Na2CO3, dried with MgSO4 and concentrated. The crude was dissolved in THF and MeOH (1 ml) was added followed by K2CO3 (4.8 g, 35.07 mmol, 2.5 eq.). After 30 min of stirring, water was added and the reaction was extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated. (6-bromo-3-fluoropyridin-2-yl)methanol (2.54 g, 79% yield) was obtained as a yellow solid.

後処理

  1. temperaturerefluxed for 2 hrs
  2. customThe solvent was evaporated
  3. additionthe residue diluted with DCM and basified with sat. aqueous Na2CO3
  4. customThe organic layers was separated
  5. washwashed with sat. aqueous Na2CO3
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. dissolutionThe crude was dissolved in THF
  9. additionMeOH (1 ml) was added
  10. stirringAfter 30 min of stirring
  11. extractionthe reaction was extracted with EtOAc
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-cd47fbba0a7e4a3192525d2e486cd5a7
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

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