Water → 2-Cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilide

HRID 439555ノート

反応式

HRID 439555 の反応式
[C:1]([C:3](=[CH:13][C:14]1[CH:19]=[C:18]([O:20]C)[C:17]([OH:22])=[C:16]([Cl:23])[CH:15]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].B(Br)(Br)Br.O>C(Cl)Cl>[C:1]([C:3](=[CH:13][C:14]1[CH:19]=[C:18]([OH:20])[C:17]([OH:22])=[C:16]([Cl:23])[CH:15]=1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:5])#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 541812382-Cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide

生成物 1

HCID 542762882-Cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilide収率 80.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide (340 mg, 1.03 mmol) in methylene chloride (20 ml) chilled at -70° C. was dropwise added 1M solution of boron tribromide in methylene chloride (2.50 ml, 2.5 mmol). The reaction mixture was gradually allowed to warm to room temperature and poured into water. The product was extracted with ethyl acetate, dried over MgSO4 and concentrated. The resulting solid was suspended in diethyl ether, refluxed for 10 minutes and the resultant solid was filtered to give the objective 2-cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilide (260 mg, 80% in yield).

後処理

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. temperaturerefluxed for 10 minutes
  5. filtrationthe resultant solid was filtered

出典と根拠

ORDレコード
ord-340296bba2ae42fa9afe4b5852d2e0bb
出典データセット
uspto-grants-1996_05
特許番号
US05514711

反応ノート

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