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

HRID 2181835노트

반응식

HRID 2181835 반응식
[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)=[CH:23][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:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[CH3:2]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823306-Ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

생성물 1

HCID 104300394-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol수율 94%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.51 g, 1.3 mmol), tetrabutylammonium iodide (1.2 g, 3.2 mmol), and 1 M boron trichloride in dichloromethane (9.0 mL, 9.0 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 2:3 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane, to yield 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a solid (0.36 g, 94%), m.p. 151° C.;

후처리

  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 2:3 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

출처 및 근거

ORD 기록
ord-877d7ea711f94528a1491dd9881dc3cd
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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