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

HRID 343397ノート

反応式

HRID 343397 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-1780b3c978684789bab313d02a56ca10
出典データセット
uspto-grants-1999_01
特許番号
US05861401

反応ノート

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