Phosphorus tribromide → 2-Bromo-4-(bromomethyl)-1-chlorobenzene

HRID 626415Notes

Reaction equation

HRID 626415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Br)(Br)[Br:12]>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][Br:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 50998689(3-Bromo-4-chlorophenyl)methanol

Product 1

HCID 509986962-Bromo-4-(bromomethyl)-1-chlorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

260 g (about 1.05 mol) of crude (3-bromo-4-chlorophenyl)methanol were dissolved in 2.86 liters of dichloromethane, the solution was cooled to −5° C. and 127.1 g (44.6 ml, 460 mmol) of phosphorus tribromide were added slowly. After the end of the addition, the mixture was stirred at −5° C. for another 1 h and then diluted with diluted with dichloromethane and water. The organic phase was removed, dried over magnesium sulphate and concentrated under reduced pressure. This gave, as a crude product, 280.5 g (about 84% of theory) of 2-bromo-4-(bromomethyl)-1-chlorobenzene.

Workup

  1. additionAfter the end of the addition
  2. additiondiluted
  3. customThe organic phase was removed
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be622ce1c1f241dda1266c2681037594
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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