Phosphorus tribromide → 1-Bromo-4-(1-bromoethyl)benzene

HRID 883920Notes

Reaction equation

HRID 883920 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Br:12])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 953521-(4-Bromophenyl)ethanol

Product 1

HCID 98381461-Bromo-4-(1-bromoethyl)benzeneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(4-bromo-phenyl)-ethanol (4.21 g, 20.9 mmol) in 15 mL of CH2Cl2 was reacted with 15 mL of 1.0M PBr3 in CH2Cl2 at room temperature for 4 h. Quenched by pouring into ice and adjusted to pH 9 with 5% aqueous NaHCO3. Extracted with CH2Cl2 and dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (4.1 g, 75%).

Workup

  1. customQuenched
  2. additionby pouring into ice
  3. extractionExtracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e9961fe2198549f28fba78820db276a0
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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