Methanol → Methyl 5-bromo-6-(isobutylthio)picolinate

HRID 624855ノート

反応式

HRID 624855 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[S:8][CH2:9][CH:10]([CH3:12])[CH3:11].S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:21])=[O:14])=[N:6][C:7]=1[S:8][CH2:9][CH:10]([CH3:12])[CH3:11]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 710874375-Bromo-6-(isobutylthio)picolinic acid

生成物 1

HCID 71087205Methyl 5-bromo-6-(isobutylthio)picolinate収率 39%

反応条件

温度
80 °C

実験手順

5-Bromo-6-(isobutylthio)picolinic acid (500 mg, 1.72 mmol) was dissolved in methanol (5 mL) to give a yellow solution. Sulfuric acid (169 mg, 92.3 μL, 1.72 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 1 d. The reaction mixture was cooled to 0° C. and poured onto ice-water/brine (25 mL). The aqueous layer was extracted with EtOAc (2×40 mL) and washed with ice-water/brine (20 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give crude title compound as a yellow oil. The oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane) to give the title product (205 mg, 39%) as a colorless oil. MS (EI): m/e=306.3 [M+H]+.

後処理

  1. customto give a yellow solution
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additionpoured onto ice-water/brine (25 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×40 mL)
  5. washwashed with ice-water/brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give crude title compound as a yellow oil
  9. customThe oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane)

出典と根拠

ORDレコード
ord-fbce10cae94342bd8399490c5d7be23b
出典データセット
uspto-grants-2016_04
特許番号
US09303012B2

反応ノート

読み込み中…