Diethyl Ether → 4-Bromo-3,5-dimethylthiophene-2-carbaldehyde

HRID 127772ノート

反応式

HRID 127772 の反応式
Br[C:2]1[S:3][C:4]([CH3:9])=[C:5]([Br:8])[C:6]=1[CH3:7].C[CH2:11][O:12]CC.[Na].C([Li])CCC>CN(C)C=O>[Br:8][C:5]1[C:6]([CH3:7])=[C:2]([CH:11]=[O:12])[S:3][C:4]=1[CH3:9]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 5360545SodiumHCID 105880762,4-Dibromo-3,5-dimethylthiopheneHCID 178418339Butyllithium

生成物 1

HCID 128752694-Bromo-3,5-dimethylthiophene-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-35 °C

実験手順

15.0 G. of 2,4-dibromo-3,5-dimethylthiophene was dissolved in 250 ml. of anhydrous ether and cooled to -70° C. with stirring under argon. 24 Ml. of a 2.4 M sodium of n-butyl lithium was slowly added to the solution and the mixture was warmed to -35° C. for 10 minutes, and then cooled again to -70° C. 7.3 G. of dimethylformamide was added slowly to the mixture and the reaction mixture was warmed to room temperature for 14 hours. The resulting solution was poured into ice water, stirred for 20 minutes and extracted with ethyl ether. The ether extracts were combined, washed with an aqueous solution of 5% sodium carbonate, saturated sodium chloride solution, dried with sodium sulfate, filtered and evaporated to yield 4-bromo-3,5-dimethylthiophene-2-carboxaldehyde, m.p. 44°-45° C.

後処理

  1. temperaturecooled again to -70° C
  2. temperaturethe reaction mixture was warmed to room temperature for 14 hours
  3. stirringstirred for 20 minutes
  4. extractionextracted with ethyl ether
  5. washwashed with an aqueous solution of 5% sodium carbonate, saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-326d6568da324d3eb077e50c391191da
出典データセット
uspto-grants-1981_03
特許番号
US04256878

反応ノート

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