Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

HRID 515362노트

반응식

HRID 515362 반응식
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]

참가 물질

3

반응물 2

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

생성물 1

HCID 13675396Diethyl 3-Nitrobenzylphosphonate수율 63.2%

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f5d4e3ab923b4cd2894c8198177f9663
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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