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

HRID 252246

반응식

HRID 252246 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 866167172,6-Dimethylbiphenyl-4-sulfonyl chloride수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01e64ea572504516919410a0628684f0
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868030B2

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