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

HRID 385722ノート

反応式

HRID 385722 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-868f88ee52db49e3b56337e79c238a3f
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

読み込み中…