Carbon tetrabromide → Di-tert-butyl phosphorobromidate

HRID 340984

반응식

HRID 340984 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 10934607Di-tert-butyl phosphorobromidate수율 172.1%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매3회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1c3517be362148f69b09218a69a17384
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895582B2

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