Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

HRID 515362ノート

反応式

HRID 515362 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O-:11])=[O:10]

参加物

3

反応物 2

HCID 31215Triethyl phosphiteHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

生成物 1

HCID 13675396Diethyl 3-Nitrobenzylphosphonate収率 63.2%

反応条件

温度
100 °C

実験手順

A stirring suspension of 1-(bromomethyl)-3-nitrobenzene (46.3 mmol, 10 g) in triethyl phosphite (69.4 mmol, 12.08 mL, 11.54 g) was heated at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and partitioned between water and dichloromethane. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: 0-5% methanol in dichloromethane) to afford the title compound (8 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica column chromatography (eluent: 0-5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-f5d4e3ab923b4cd2894c8198177f9663
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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