(Diethylamino)sulfur trifluoride → 5-Bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzene

HRID 638946ノート

反応式

HRID 638946 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:12][CH3:13])=[C:6]([CH:8](O)[CH2:9][CH3:10])[CH:7]=1.CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:12][CH3:13])=[C:6]([CH:8]([F:22])[CH2:9][CH3:10])[CH:7]=1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 14470708HCID 14470708、化合物

生成物 1

HCID 686856045-Bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzene収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1-(5-bromo-2,3-dimethoxyphenyl)propan-1-ol (400 mg, 1.45 mmol) in DCM (10 mL) at −78° C. was added DAST (0.58 mL, 4.36 mmol) and stirred the reaction for 10 min at −78° C., then warmed to 0° C. for 2 h. The reaction was quenched with water and saturated aqueous NH4Cl (100 mL), extracted with EtOAc, dried over NasSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel using 30% EtOAc in hexanes as an eluent to furnish 5-bromo-1-(1-fluoropropyl)-2,3-dimethoxybenzene (80%).

後処理

  1. customthe reaction for 10 min at −78° C.
  2. customThe reaction was quenched with water and saturated aqueous NH4Cl (100 mL)
  3. extractionextracted with EtOAc
  4. customdried over NasSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica gel using 30% EtOAc in hexanes as an eluent

出典と根拠

ORDレコード
ord-6c80cc6a6fbe4320ae9c060d4bcdb4ec
出典データセット
uspto-grants-2010_04
特許番号
US07691843B2

反応ノート

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