Benzoyl Peroxide → Diethyl [(1E)-3-bromoprop-1-en-1-yl]phosphonate

HRID 2051962ノート

反応式

HRID 2051962 の反応式
[CH:1](/[P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])=[CH:2]\[CH3:3].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:3]/[CH:2]=[CH:1]/[P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5702572Diethyl (1E)-prop-1-en-1-ylphosphonate

生成物 1

HCID 5702525Diethyl [(1E)-3-bromoprop-1-en-1-yl]phosphonate収率 58.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of diethyl trans-1-propenylphosphonate (32.04 g.) in carbon tetrachloride (320 ml.) were added N-bromosuccinimide (41.65 g.) and dibenzoylperoxide (2.8 g.). The reaction mixture was heated to reflux for 1.5 hours and stirred for 30 minutes under ice-cooling. Insoluble materials were removed off by filtration and the filtrate was concentrated under reduced pressure to give an oily residue (63.09 g.), which was subjected to a column chromatography on silicagel and eluted with chloroform. The eluates were evaporated to dryness under reduced pressure to give an oily diethyl 3-bromo-trans-1-propenylphosphonate (27.04 g.).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooling
  4. customInsoluble materials were removed off by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give an oily residue (63.09 g.), which
  7. washeluted with chloroform
  8. customThe eluates were evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-9363f1fddaf74e7e887f8ec6a2a96546
出典データセット
uspto-grants-1980_01
特許番号
US04182758

反応ノート

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