Toluene → 5-(chlorosulfonyl)-2-methoxyphenyl Methanesulfonate

HRID 2140

반응식

HRID 2140 반응식
[CH3:1][S:2]([O:5]COC1C=CC=CC=1)(=[O:4])=[O:3].[Cl:14][S:15]([OH:18])(=O)=[O:16].C(Cl)(=O)[C:20](Cl)=[O:21].[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.CN(C=O)C>[CH3:1][S:2]([O:5][C:26]1[CH:27]=[C:28]([S:15]([Cl:14])(=[O:18])=[O:16])[CH:29]=[CH:30][C:25]=1[O:21][CH3:20])(=[O:4])=[O:3]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chloride2회HCID 196896432-(Methanesulphonyloxy)methoxybenzene

생성물 1

HCID 196896415-(chlorosulfonyl)-2-methoxyphenyl Methanesulfonate

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매3회

반응 조건

온도
-10 °C

실험 절차

A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixture was stirred for a further 4 hours, allowing the temperature to rise to 10° C. The mixture was evaporated to dryness in vacuo to yield an oil which was suspended in toluene (20 ml) with stirring under a nitrogen atmosphere. Oxalyl chloride (0.36 ml) was added dropwise, followed by the addition of DMF (5 drops). After stirring for 2 hours at room temperature, dichloromethane (15 ml) and oxalyl chloride (0.36 ml) were added and the reaction stirred overnight. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with 60% ethyl acetate in hexane to furnish the title compound (0.99 g) as a white crystalline solid.

후처리

  1. temperaturemaintaining the temperature below 0° C
  2. customto rise to 10° C
  3. customThe mixture was evaporated to dryness in vacuo
  4. customto yield an oil which
  5. stirringwith stirring under a nitrogen atmosphere
  6. stirringAfter stirring for 2 hours at room temperature
  7. stirringthe reaction stirred overnight
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was purified by column chromatography on silica
  10. washeluting with 60% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-0c015ee7e7924c23b9f14267ea629a04
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728712

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