Dimethyl Sulfate → 5-Bromo-3-cyclobutyl-2-methoxybenzaldehyde

HRID 385048ノート

反応式

HRID 385048 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:15](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[C:5]([O:10][CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 866681565-Bromo-3-cyclobutyl-2-hydroxybenzaldehyde

生成物 1

HCID 866681575-Bromo-3-cyclobutyl-2-methoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-bromo-3-cyclobutyl-2-hydroxybenzaldehyde was dissolved in N,N-dimethylformamide (30 mL), and potassium carbonate (10.79 g) and dimethylsulfuric acid (3.7 mL) were added to the solution under water cooling, and then the mixture was stirred at room temperature for 14 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain the title compound (1.27 g) as a yellow oily substance.

後処理

  1. filtrationThe reaction solution was filtered
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-caf19eecd7774e679e70d6ddfa5d7e6a
出典データセット
uspto-grants-2013_02
特許番号
US08367843B2

反応ノート

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