Dichloromethane → 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol

HRID 2181837ノート

反応式

HRID 2181837 の反応式
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([CH3:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482394HCID 22482394、化合物

生成物 1

HCID 100008734-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol収率 50%

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.53 g, 1.3 mmol), tetrabutylammonium iodide (1.2 g, 3.2 mmol), and 1 M boron trichloride in dichloromethane (8.9 mL, 8.9 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 1:1 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane to yield 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol as a homogeneous solid (0.25 g, 50%), m.p. 181° C.;

後処理

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 1:1 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

出典と根拠

ORDレコード
ord-7507716b22c245998a7cefe0f1b35f2d
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

反応ノート

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