1,3-Dibromopropane → 1-(3-Bromopropoxy)-3-nitrobenzene

HRID 533853ノート

反応式

HRID 533853 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:14][CH2:13][CH2:12][Br:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 111373-Nitrophenol

生成物 1

HCID 71723011-(3-Bromopropoxy)-3-nitrobenzene収率 56.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-nitrophenol (0.0689 g, 0.495 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.500 mL, 3.05 mmol) followed by Cs2CO3 (0.244 g, 0.748 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0730 g, 56.6%). EI-MS Rt (2.20 min).

後処理

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (4 mL)
  3. extractionextracted with DCM (8 mL)
  4. customThe organic layer was dried through a phase separator
  5. concentrationconcentrated under vacuum
  6. custompurified by preparatory HPLC (without TFA)

出典と根拠

ORDレコード
ord-48bd893f73004105b8bc2e9cd0ab3056
出典データセット
uspto-grants-2014_10
特許番号
US08853404B2

反応ノート

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