(Diethylamino)sulfur trifluoride → 3-(4-Bromophenyl)-3-fluorooxetane

HRID 385722노트

반응식

HRID 385722 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:19])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:19])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 583823793-(4-Bromophenyl)oxetan-3-ol

생성물 1

HCID 595256233-(4-Bromophenyl)-3-fluorooxetane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

3-(4-Bromophenyl)oxetan-3-ol (1.55 g, 6.77 mmol) was taken up in DCM (100 mL) and cooled to −78° C. DAST (1.073 mL, 8.12 mmol) was added and the mixture was stirred at −78° C. for 90 minutes followed by 0° C. for 20 minutes. Saturated NaHCO3 was added and the products extracted into DCM (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a yellow oil.

후처리

  1. waitfollowed by 0° C. for 20 minutes
  2. extractionthe products extracted into DCM (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-868f88ee52db49e3b56337e79c238a3f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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