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

HRID 11988

反応式

HRID 11988 の反応式
[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

参加物

5

反応物 2

HCID 271446-Bromo-2-naphthalenolHCID 31398Chlorosuccinimide

生成物 1

HCID 220481596-Bromo-1-chloronaphthalen-2-ol収率 95.4%

試薬・触媒・溶媒 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8195caeae8504cdfb40a16fc4ca39ca5
出典データセット
uspto-grants-2010_06
特許番号
US07727417B2

関連ノート

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