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

HRID 439555노트

반응식

HRID 439555 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-340296bba2ae42fa9afe4b5852d2e0bb
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514711

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