Pyridine → 2-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate

HRID 2403711ノート

反応式

HRID 2403711 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[CH2:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1.N1C=CC=CC=1.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].CC(=O)OCC>C(Cl)Cl.O>[CH3:33][C:32]1[CH:34]=[CH:35][C:29]([S:26]([O:15][CH2:14][CH2:13][O:12][C:11]2[CH:16]=[CH:17][C:8]([CH2:7][C:6]3[CH:18]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[Cl:19])=[CH:9][CH:10]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 595577842-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethanol2 回

生成物 1

HCID 595577472-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate収率 81.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethanol (intermediate I) (3.41 g) in anhydrous DCM (20 mL), pyridine (2.0 eq) was added, and then the mixture was stirred and cooled to 0° C. Then TsCl (1.3 eq) was added in portions, and the mixture was allowed to warmed to room temperature and stirred overnight. TLC (PE:EA=4:1) showed the reaction was complete. Then the mixture was poured into water and extracted with DCM, washed with water and brine, and dried with anhydrous Na2SO4. The solvent was then evaporated under reduced pressure, and the solid crude product was purified by column chromatography (PE:EA=30:1) to obtain intermediate AB (4.05 g, yield 81.7%).

後処理

  1. temperatureto warmed to room temperature
  2. stirringstirred overnight
  3. extractionextracted with DCM
  4. washwashed with water and brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customThe solvent was then evaporated under reduced pressure
  7. customthe solid crude product was purified by column chromatography (PE:EA=30:1)
  8. customto obtain intermediate AB (4.05 g, yield 81.7%)

出典と根拠

ORDレコード
ord-3e51e2bf03fa46238ea90b3506137e6a
出典データセット
uspto-grants-2014_08
特許番号
US08802637B2

反応ノート

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