Triethyl phosphite → Diethyl 3-Bromobenzylphosphonate

HRID 662094

反応式

HRID 662094 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].P([O-])([O-])[O-]>>[CH2:12]([O:11][P:10]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:13]

参加物

4

反応物 3

HCID 31215Triethyl phosphiteHCID 699793-Bromobenzyl bromideHCID 107908Phosphite

生成物 1

HCID 10979718Diethyl 3-Bromobenzylphosphonate

反応条件

温度
130 °C

実験手順

To 1-bromo-3-(bromomethyl)benzene (100 g, 400 mmol) in a 500 mL round-bottom flask under nitrogen was added triethyl phosphite (69.6 mL, 400 mmol) and the solution was heated to 130° C. The apparatus was set up ready for distillation. As the heating block reached 130° C. the mixture began to reflux and a large volume of colourless liquid was allowed to distill off. Lab HPLC of the reaction after 40 min showed some starting material so another 0.5 eq of the phosphite was added, and heating with distillation continued. The reaction was then heated under vacuum and the excess phosphite was distilled off under vacuum (130° C. heater and 15 mbar, gradually going down to 0.5 mbar). This gave 120.8 g (98%) of a colourless oil that the lab HPLC showed to be 97% pure with a 2.20 min retention time. LC-MS m/z 307, 309 (M+H)+, 1.01 min (ret time).

後処理

  1. distillationThe apparatus was set up ready for distillation
  2. customreached 130° C.
  3. temperatureto reflux
  4. distillationto distill off
  5. customLab HPLC of the reaction after 40 min
  6. additionwas added
  7. temperatureheating with distillation
  8. temperatureThe reaction was then heated under vacuum
  9. distillationthe excess phosphite was distilled off under vacuum (130° C. heater and 15 mbar
  10. custompure with a 2.20 min
  11. customLC-MS m/z 307, 309 (M+H)+, 1.01 min (ret time)

出典と根拠

ORDレコード
ord-baf05bdce177423ca6fa6d36d7e6ac49
出典データセット
uspto-grants-2011_12
特許番号
US08084449B2

関連ノート

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