Bromine → 4-Bromo-5-chloro-2-cyanophenol

HRID 326582노트

반응식

HRID 326582 반응식
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:14]#[N:15])=[C:11]([OH:13])[CH:12]=1.[Br:16]Br>CO>[Br:16][C:8]1[C:7]([Cl:6])=[CH:12][C:11]([OH:13])=[C:10]([C:14]#[N:15])[CH:9]=1

참가 물질

5

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 34427894-Chloro-2-hydroxybenzonitrile

생성물 1

HCID 197351294-Bromo-5-chloro-2-cyanophenol수율 23.8%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
-78 °C

실험 절차

Methanol (100 ml) was added to sodium acetate (1.97 g) and 5-chloro-2-cyanophenol (1.84 g, mp. 155°-157° C.) which was synthesized according to a known method. The mixture was allowed to cool to -78° C., and to the solution was added dropwise a solution of bromine (1.53 g) in methanol (25 ml). After stirring at -78° C. for 30 minutes, the solvent was distilled off under reduced pressure, and ethyl acetate and aqueous potassium bisulfate solution were added to the residue. The ethyl acetate layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane to obtain 4-bromo-5-chloro-2-cyanophenol (0.53 g, mp. 229°-231° C. (dec.)).

후처리

  1. customwas synthesized
  2. distillationthe solvent was distilled off under reduced pressure, and ethyl acetate and aqueous potassium bisulfate solution
  3. additionwere added to the residue
  4. washThe ethyl acetate layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-a42bd111b63846aa9d096adabfea41f4
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270308

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