6-Bromo-2-naphthalenol → 6-Bromo-1-chloronaphthalen-2-ol

HRID 11988

반응식

HRID 11988 반응식
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]2>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-].ClCCl>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([Cl:1])=[C:15]([OH:20])[CH:14]=[CH:13]2

참가 물질

5

반응물 2

HCID 271446-Bromo-2-naphthalenolHCID 31398Chlorosuccinimide

생성물 1

HCID 220481596-Bromo-1-chloronaphthalen-2-ol수율 95.4%

시약·촉매·용매 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

The synthesis of (S1-2) was carried out following the method described in Synlett, No. 18, 2837 (2005), wherein 29.9 g of N-chlorosuccinimide and 600 ml of dichloromethane were added to a reactor in nitrogen atmosphere and cooled to 0° C., 2.6 g of zirconium (IV) chloride was added, and then 50 g of 6-bromo-2-naphthol (S1-1) was added slowly. The reaction solution was heated to room temperature and stirred for 10 hours, then washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate, and distilled under a reduced pressure to remove the solvent. Recrystallization was carried out using a mixed solvent of toluene/heptane=1/1 (volumetric ratio) to obtain 55 g of 6-bromo-1-chloro-2-naphthol (S1-2).

후처리

  1. customThe synthesis of (S1-2)
  2. temperatureThe reaction solution was heated to room temperature
  3. washwashed with saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled under a reduced pressure
  6. customto remove the solvent
  7. customRecrystallization

출처 및 근거

ORD 기록
ord-8195caeae8504cdfb40a16fc4ca39ca5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727417B2

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