Sulfur Dioxide → 2,6-Dimethylbiphenyl-4-sulfonyl chloride

HRID 252246

反応式

HRID 252246 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH3:20])[CH:8]=1.S(=O)=O.[S:24](Cl)([Cl:27])(=[O:26])=[O:25]>O1CCCC1.CCCCCC>[CH3:13][C:11]1[CH:12]=[C:7]([S:24]([Cl:27])(=[O:26])=[O:25])[CH:8]=[C:9]([CH3:20])[C:10]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 1119Sulfur DioxideHCID 24648Sulfuryl chlorideHCID 668578334-Bromo-2,6-dimethylbiphenylHCID 178418339Butyllithium

生成物 1

HCID 866167172,6-Dimethylbiphenyl-4-sulfonyl chloride収率 74%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

2.5 M n-butyllithium, in tetrahydrofuran, (0.46 ml, 1.17 mmol, 1.1 equiv.) was added dropwise to a solution of 4-bromo-2,6-dimethylbiphenyl (0.28 g, 1.06 mmol, 1.0 equiv.) in dry tetrahydrofuran (5 ml), under nitrogen at −78° C. and the mixture stirred for 15 minutes. This solution was added, by canula, to a solution of sulfur dioxide (3 mL) and tetrahydrofuran (3 ml) under nitrogen at −78° C. The solution was allowed to warm to room temperature while stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue suspended in hexane (4 ml) and dichloromethane (4 ml). The suspension was cooled to 0° C., a solution of sulfuryl chloride (0.14 g, 1.06 mmol, 1.0 equiv.) in hexane (2 ml) was added and the mixture was allowed to warm to room temperature while stirring for 1.5 hours. The hexane and dichloromethane were evaporated under reduced pressure to afford crude 2,6-dimethylbiphenyl-4-sulfonyl chloride, 0.22 g (74% yield) as a red gum, this material was used in the next step without further purification.

後処理

  1. stirringwhile stirring for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureThe suspension was cooled to 0° C.
  4. temperatureto warm to room temperature
  5. stirringwhile stirring for 1.5 hours
  6. customThe hexane and dichloromethane were evaporated under reduced pressure

出典と根拠

ORDレコード
ord-01e64ea572504516919410a0628684f0
出典データセット
uspto-grants-2011_01
特許番号
US07868030B2

関連ノート

読み込み中…