Dichloromethane → 3-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181853ノート

反応式

HRID 2181853 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27]

参加物

5

反応物 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822658-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

生成物 1

HCID 99763533-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol収率 77%

実験手順

The title compound was prepared from 8-fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.50 g, 1.3 mmol), cyclohexene (2.4 mL, 24 mmol), and 1 M boron tribromide in dichloromethane (7.8 mL, 7.8 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4), followed by trituration from hexane, to yield 3-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.37 g, 71%), m.p. 161° 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 (1:4)

出典と根拠

ORDレコード
ord-847732f1ef5c41d18951a69d66792943
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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