Toluene → Prop-2-ynyl-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine

HRID 1260342노트

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HRID 1260342 반응식
[F:1][C:2]1([F:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:5]=2[O:4][C:3]1([F:14])[F:13].[CH2:16](Br)[C:17]#[CH:18].C1(C)C=CC=CC=1>FC1C=CC=CC=1>[CH2:18]([NH:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([F:1])([F:15])[C:3]([F:13])([F:14])[O:4][C:5]=2[CH:11]=1)[C:17]#[CH:16]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 7842Propargyl bromideHCID 27765742,2,3,3-Tetrafluoro-1,4-benzodioxin-6-amine

생성물 1

HCID 86619165Prop-2-ynyl-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine

시약·촉매·용매 1

HCID 10008Fluorobenzene용매

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온도
50 °C

실험 절차

2,2,3,3-Tetrafluoro-6-aminobenzodioxane (6.694 g, 30.0 mmol) and Aldrich basic alumina (activated, Brockmann 1, 150 mesh, CAS#1344-28-1) (51 g) were mixed in fluorobenzene (100 mL) and then treated with 80% propargyl bromide in toluene (2.56 mL, 23.0 mmol). The resulting mixture was thoroughly stirred and heated at 50° C. for 17 hours. The mixture was cooled to ambient temperature and filtered. The alumina was rinsed thoroughly with dichloromethane (150 mL), the filtrate was reduced in volume under reduced pressure, washed with concentrated aqueous NH4OH (5 mL), dried (Na2SO4), concentrated and chromatographed on silica eluting with 0-10% EtOAc/hexanes to provide the titled compound. 1H NMR (CDCl3) δ ppm 2.24 (t, 1H), 3.92 (m, 2H), 3.96 (m, 1H), 6.43 (d, 1H), 6.45 (dd, 1H), 6.96 (d, 1H); MS (DCI) 262 (M+H).

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washThe alumina was rinsed thoroughly with dichloromethane (150 mL)
  4. washwashed with concentrated aqueous NH4OH (5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed on silica eluting with 0-10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-a8b9a44aed464dd2a86176d50426552a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470813B2

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