Carbon tetrabromide → Di-tert-butyl phosphorobromidate

HRID 409846

反応式

HRID 409846 の反応式
C(Br)(Br)(Br)[Br:2].[OH-].[Na+].[C:8]([O:12][P:13]([O-:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])([CH3:10])[CH3:9].P([O-])([O-])[O-]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[P:13]([Br:2])(=[O:19])([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

参加物

7

反応物 4

HCID 11205Carbon tetrabromideHCID 14798Sodium HydroxideHCID 107908PhosphiteHCID 21959072Di-tert-butyl phosphite

生成物 1

HCID 10934607Di-tert-butyl phosphorobromidate収率 172.1%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A 500 mL 3-neck flask equipped with dropping funnel and thermometer was charged with carbon tetrabromide (16.58 g, 50 mmol), benzyltriethylammonium chloride (1.14 g, 5.0 mmol) and dichloromethane (50 mL). A 20% w/w NaOH solution (50 mL) was added with vigorous stirring, followed by dropwise addition of a solution of di-tert-butylphosphite (20 g, 100 mmol) in dichloromethane (20 mL), the rate of addition was controlled to keep the temperature of reaction mixture not to exceed to 25° C. After addition of phosphite, the mixture was further stirred at room temperature for 3 h, diluted with dichloromethane (20 mL) and separated. The organic phase was washed with saturated sodium bisulfite, water, brine, dried (Na2SO4), filtered and concentrated at RT. After removing the solvent, the residue was further pumped in vacuo for 1 h to give di-tert-butyl phosphorobromidate as a colorless oil (23.5 g, 86%).

後処理

  1. customA 500 mL 3-neck flask equipped
  2. additionthe rate of addition
  3. customthe temperature of reaction mixture not
  4. customto exceed to 25° C
  5. customseparated
  6. washThe organic phase was washed with saturated sodium bisulfite, water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated at RT
  10. customAfter removing the solvent
  11. waitthe residue was further pumped in vacuo for 1 h

出典と根拠

ORDレコード
ord-31f60f9378ee447489fcbff3e6905ad4
出典データセット
uspto-grants-2014_06
特許番号
US08759374B2

関連ノート

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