Phosphorus tribromide → HCID 18408353, compound

HRID 1385916Notes

Reaction equation

HRID 1385916 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:5]([CH2:6]O)=[C:4]([F:14])[CH:3]=1.P(Br)(Br)[Br:16]>C(OCC)C>[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:5]([CH2:6][Br:16])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 21200446HCID 21200446, compound

Product 1

HCID 18408353HCID 18408353, compoundYield 254%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

124 g (0.56 mol) of 4-chloro-2-fluoro-5-isopropoxybenzyl alcohol was dissolved in 900 ml of diethyl ether, and 55 g (0.20 mol) of phosphorus tribromide was dropwise added thereto under cooling with ice. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water and extracted with diethyl ether. The extract was washed with water and an aqueous sodium hydrogencarbonate solution, and then, the organic layer was dried over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure to obtain 143 g (yield: 89%) of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialan aqueous sodium hydrogencarbonate solution, and then, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationDiethyl ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-850faf3d11ff437e944ac7c49e911035
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

Loading…