Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

HRID 511209ノート

反応式

HRID 511209 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O-:3])=[O:2]

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 98%

反応条件

温度
140 °C

実験手順

A mixture of 3-nitrobenzyl bromide (648 mg, 3.00 mmol) and triethyl phosphite (0.669 mL, 3.90 mmol) was stirred at 140° C. under nitrogen for 16 h. The excess triethyl phosphite was removed under reduced pressure and the residue purified by chromatography over silica gel eluting with 2% MeOH in dichloromethane to afford diethyl (3-nitrobenzyl)phosphonate, 0.80 g (yield: 98%). 1H-NMR (CD3OD, 400 MHz): δ=1.27 (t, J=6.8 Hz, 6 H), 3.43 (d, J=22.0 Hz, 2 H), 4.08 (q, J=6.8 Hz, 4 H), 7.58 (t, J=8.0 Hz, 1 H), 7.72 (d, J=7.6 Hz, 1 H), 8.15 (d, J=8.4 Hz, 1 H), 8.22 (d, J=2.4 Hz, 1 H). MS (ES+): m/z 273.99 (MH+). HPLC: tR=2.92 min (ZQ3, polar—5 min).

後処理

  1. customThe excess triethyl phosphite was removed under reduced pressure
  2. customthe residue purified by chromatography over silica gel eluting with 2% MeOH in dichloromethane

出典と根拠

ORDレコード
ord-2d113f11fe4e4cddb578b69490e086aa
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

反応ノート

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