Oxalyl chloride → 4,6-Dimethylbenzothiophene-2,3-dione

HRID 388462

反応式

HRID 388462 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[CH:7]=[C:8]([SH:13])[CH:9]=[C:10]([CH3:12])[CH:11]=1.[C:14](Cl)(=[O:18])[C:15](Cl)=[O:16]>C(Cl)Cl>[CH3:12][C:10]1[C:9]2[C:15](=[O:16])[C:14](=[O:18])[S:13][C:8]=2[CH:7]=[C:6]([CH3:5])[CH:11]=1

参加物

5

反応物 3

HCID 65578Oxalyl chlorideHCID 1175483,5-DimethylbenzenethiolHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 584974374,6-Dimethylbenzothiophene-2,3-dione収率 36.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of AlCl3(0.4 g, 3.6 mmol) in CH2Cl2 (4 mL) at −20° C. under nitrogen are added 3,5-dimethylbenzenethiol (1 g, 7.2 mmol) and oxalyl chloride (0.6 mL, 7.2 mmol) respectively. The solution is warmed to room temperature for 1 hour and is heated to 120° C. in a microwave reactor for 15 minutes. The solution is cooled and is poured into crushed ice. The solution is extracted with CH2Cl2 and the organic layer is collected. The solution is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent to afford 4,6-dimethyl-benzo[b]thiophene-2,3-dione (500 mg, 35%).

後処理

  1. temperatureis heated to 120° C. in a microwave reactor for 15 minutes
  2. temperatureThe solution is cooled
  3. additionis poured
  4. custominto crushed ice
  5. extractionThe solution is extracted with CH2Cl2
  6. customthe organic layer is collected
  7. dry with materialThe solution is dried with MgSO4
  8. filtrationis filtered
  9. concentrationThe filtrate is concentrated
  10. customthe residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

出典と根拠

ORDレコード
ord-60e5c30b5e09448abd3291c410b6c9dc
出典データセット
uspto-grants-2013_02
特許番号
US08377949B2

関連ノート

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