Phosphorus tribromide → 3-(1-(Benzyloxyimino)ethyl)benzylbromide

HRID 2296970Notes

Reaction equation

HRID 2296970 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]O)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:21]>C(OCC)C>[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][Br:21])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 867586303-(1-(Benzyloxyimino)ethyl)benzylalcohol

Product 1

HCID 734333223-(1-(Benzyloxyimino)ethyl)benzylbromideYield 194.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.55 g (10 mmol) of 3-(1-(benzyloxyimino)ethyl)benzylalcohol in 20 ml of dry diethyl ether was added dropwise 1.35 g (4.5 mmol) of phosphorous tribromide with ice-cooling. The mixture was removed from an ice bath and stirred at room temperature for 6 hours. To the reaction mixture were added ice water and diethyl ether. The mixture was stirred for 30 minutes and separated. The organic layer was washed successively with an about 5% aqueous solution of sodium bicarbonate and water, then dried and concentrated to obtain 2.78 g (8.74 mmol) of 3-(1-(benzyloxyimino)ethyl)benzylbromide.

Workup

  1. temperaturecooling
  2. customThe mixture was removed from an ice bath
  3. additionTo the reaction mixture were added ice water and diethyl ether
  4. stirringThe mixture was stirred for 30 minutes
  5. customseparated
  6. washThe organic layer was washed successively with an about 5% aqueous solution of sodium bicarbonate and water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9185698488d54e1086fed725b3e01fad
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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