2,4-Difluorobenzaldehyde → 4-Fluoro-2-(methylthio)benzaldehyde

HRID 1618014ノート

反応式

HRID 1618014 の反応式
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][S-:12].[Na+]>C1(C)C=CC=CC=1>[F:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([S:12][CH3:11])[CH:9]=1

参加物

4

反応物 2

HCID 737702,4-DifluorobenzaldehydeHCID 4378561Sodium methanethiolate

生成物 1

HCID 219474094-Fluoro-2-(methylthio)benzaldehyde収率 37.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2,4-difluorobenzaldehyde (3.0 g, 21.1 mmol, CAS RN 1550-35-2) in toluene (29 mL) was added sodium thiomethoxide (2.03 g, 28.9 mmol) and the resulting suspension was stirred at 80° C. for 7 hours. Heating was removed and stirring continued at room temperature for another 18 hours. The reaction mixture was treated with diethyl ether (50 mL) and water (15 mL) and the layers were separated. The aqueous layer was extracted twice with ethyl acetate (50 mL each). The organic layers were washed with saturated aqueous sodium hydrogencarbonate solution and with brine, dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in 50 mL n-heptane and 50 mL diethyl ether and the clear solution was evaporated slowly until a turbid solution formed. The originally oily precipitation turned into a white solid which was filtered, washed with n-heptane and dried under high vacuum to give the compound as a colourless solid (1.35 g, 37%). MS (ESI+): m/z=170.0 ([M+H]+).

後処理

  1. temperatureHeating
  2. customwas removed
  3. stirringstirring
  4. waitcontinued at room temperature for another 18 hours
  5. additionThe reaction mixture was treated with diethyl ether (50 mL) and water (15 mL)
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted twice with ethyl acetate (50 mL each)
  8. washThe organic layers were washed with saturated aqueous sodium hydrogencarbonate solution and with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residue was dissolved in 50 mL n-heptane
  13. custom50 mL diethyl ether and the clear solution was evaporated slowly until a turbid solution
  14. customformed
  15. customThe originally oily precipitation
  16. filtrationwas filtered
  17. washwashed with n-heptane
  18. customdried under high vacuum

出典と根拠

ORDレコード
ord-e6d736ca674c4e2baa589c7e3e184780
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

反応ノート

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