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

HRID 1476096Notes

Reaction equation

HRID 1476096 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 mixture was cooled to −5° C. and 127.1 g (44.6 ml, 460 mmol) of phosphorous tribromide were added slowly. After the addition had ended, stirring at −5° C. was continued for 1 h, and the mixture was then diluted with dichloromethane and water. The organic phase was separated off, 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 addition
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26433e83b2254d73a0bc6fbc745d5602
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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