Phosphorus tribromide → HCID 18408353, compound

HRID 992853Notes

Reaction equation

HRID 992853 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-2f840f3cce764cb9872327845c45e610
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

Loading…