Nitric Acid → 4'-Isobutyl-3'-nitro-2-biphenylsulphonyl chloride

HRID 343397노트

반응식

HRID 343397 반응식
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7]>C(OC(=O)C)(=O)C>[CH2:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][C:14]=1[N+:1]([O-:4])=[O:2])[CH:6]([CH3:8])[CH3:7]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 108286564'-Isobutyl-2-biphenylsulphonyl chloride

생성물 1

HCID 187047904'-Isobutyl-3'-nitro-2-biphenylsulphonyl chloride

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

Fuming nitric acid (0.8 ml) was added over 10 minutes to a stirred solution of 4'-isobutyl-2-biphenylsulphonyl chloride (3.09 g) in acetic anhydride (18 ml) at -20° C. The solution was kept at -20° C. for 1.5 hours and then allowed to warm to ambient temperature. The solution was stirred for 1.5 hours and then added to ice (300 g) with vigorous stirring. The mixture was stirred for 30 minutes and extracted with ether (3×100 ml) while still below 10° C. The ethereal solution was dried (MgSO4) and the solvent was removed by evaporation. The resulting oil was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v), to give 4'-isobutyl-3'-nitro-2-biphenylsulphonyl chloride (2.01 g); 1H NMR (CDCl3): 0.95 (d,6H), 1.9-2.05 (m,1H), 2.9 (d,2H), 7.35-7.5 (m,2H), 7.6 (d,1H), 7.7 (d,1H), 7.8 (t,1H), 8.0 (s,1H), 8.25 (d,1H); mass spectrum (EI): 353(M+).

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionextracted with ether (3×100 ml) while still below 10° C
  3. dry with materialThe ethereal solution was dried (MgSO4)
  4. customthe solvent was removed by evaporation
  5. customThe resulting oil was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:9 v/v)

출처 및 근거

ORD 기록
ord-1780b3c978684789bab313d02a56ca10
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861401

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