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

HRID 2038467노트

반응식

HRID 2038467 반응식
[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

참가 물질

7

반응물 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 595577842-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethanol2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-9b001fb3e1d9475398149a84ff3c1560
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575321B2

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