Tert-Butyl nitrite → 2-Methyl-3,4-dimethylthiobromobenzene

HRID 970166ノート

反応式

HRID 970166 の反応式
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([S:16][CH3:17])[C:10]=1[CH3:18].[CH3:19][S:20]SC>[Cu]>[CH3:18][C:10]1[C:11]([S:16][CH3:17])=[C:12]([S:20][CH3:19])[CH:14]=[CH:15][C:9]=1[Br:8]

参加物

5

反応物 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl Disulfide2 回HCID 18757264HCID 18757264、化合物

生成物 1

HCID 187572682-Methyl-3,4-dimethylthiobromobenzene

試薬・触媒・溶媒 1

HCID 23978Copper触媒

反応条件

温度
50 °C

実験手順

14.8 g (129 mmol) of tert-butyl nitrite and 20 g of copper powder are initially charged in 50 ml of dimethyl disulfide, and a solution of 20 g (86 mol) of 4-bromo-3-methyl-2-methylthioaniline in 100 ml of dimethyl disulfide is added dropwise at 50-55° C. The mixture is then stirred at 50° C. for 4 hours. For work-up, the solid is filtered off with suction and the solution is diluted with methylene chloride and extracted with dilute hydrochloric acid. The organic phase is washed with saturated aqueous NaHCO3 solution, dried over sodium sulfate, filtered off and concentrated using a rotary evaporator. Excess dimethyl disulfide is removed under oil pump vacuum.

後処理

  1. filtrationFor work-up, the solid is filtered off with suction
  2. additionthe solution is diluted with methylene chloride
  3. extractionextracted with dilute hydrochloric acid
  4. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customExcess dimethyl disulfide is removed under oil pump vacuum

出典と根拠

ORDレコード
ord-858bb4c9dd8947898774f9c84808e480
出典データセット
uspto-grants-2007_12
特許番号
US07309802B2

反応ノート

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