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

HRID 2287409ノート

反応式

HRID 2287409 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].CCOCC>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

5

反応物 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 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 sextracted with ether 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. extractionextracted with ether (3×100 ml) while still below 10° C
  2. dry with materialThe ethereal solution was dried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe resulting oil was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (1:9 v/v)

出典と根拠

ORDレコード
ord-af5669d138054d0c83b92c3c5ecea140
出典データセット
uspto-grants-2000_07
特許番号
US06083951

反応ノート

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