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Dichloromethane → 2-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181866
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HRID 2181866 반응식
[F:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[CH:26]([CH3:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8]C.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[CH:26]([CH3:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)(=[O:11])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]
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참가 물질

5

반응물 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822965-[(3-Fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

생성물 1

HCID 224822772-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol수율 74%

실험 절차

The title compound was prepared from 5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.5 g, 1.3 mmol), cyclohexene (0.33 mL, 3.25 mmol) and 1.0 M boron tribromide in dichloromethane (7.8 mL, 7.8 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by flash column chromatography on silica gel, eluting sequentially with dichloromethane and ethyl acetate to yield 2-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.35 g, 0.96 mmol, 74%) as a light-yellow solid, m.p. 172-174° C.;

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting sequentially with dichloromethane and ethyl acetate

출처 및 근거

ORD 기록
ord-88b5b185ba99454390bb13a8bfcface9
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06894061B2

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