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3,4-dihydro-2H-pyran → 6-Bromo-5-(2,4-difluorophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,3-benzotriazole

HRID 629301
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인쇄 미리보기

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HRID 629301 반응식
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]2[N:9]=[N:8][NH:7][C:6]=2[CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1>C(Cl)(Cl)Cl.ClCCl>[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][O:32]3)[C:6]=2[CH:10]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178505880HCID 178505880, 화합물

생성물 1

HCID 1180936576-Bromo-5-(2,4-difluorophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,3-benzotriazole

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344
Dichloromethane
용매

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온도
60 °C

실험 절차

A solution of 6-bromo-5-(2,4-difluorophenoxy)-1H-1,2,3-benzotriazole (0.047 g, 0.14 mmol) and p-toluenesulfonic acid monohydrate (0.0027 g, 0.014 mmol) in chloroform (0.65 mL) was treated with dihydropyran (0.0197 mL, 0.216 mmol) and stirred at 60° C. for 1 h. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was separated and re-extracted with dichloromethane. The combined organic layers were separated, washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to a crude oil. Purification by flash column chromatography (100% hexanes to 60% EtOAc/hexanes) gave the desired product as a mixture of isomers that was used without further purification.

후처리

  1. washwashed with saturated sodium bicarbonate
  2. customThe aqueous layer was separated
  3. extractionre-extracted with dichloromethane
  4. customThe combined organic layers were separated
  5. washwashed with water and brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude oil
  9. customPurification by flash column chromatography (100% hexanes to 60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-15d69c2e0bf241f390ec09f8fdae1433
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315501B2

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