Bromine → 4-Bromo-2-(bromomethyl)-1-fluorobenzene

HRID 622714Notes

Reaction equation

HRID 622714 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:10]Br>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH2:8][Br:10])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1235275-Bromo-2-fluorotoluene

Product 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a refluxing solution of 5-bromo-2-fluorotoluene (3.8 g, 20 mmol) in CCl4 (30 mL) illuminated with a 275 W UV-sun lamp, a solution of Br2 (1.1 mL, 20 mmol) in CCl4 (30 mL) was added dropwise. Refluxing and irradiation were continued for an additional 0.5 h and then the clear pale amber solution was concentrated. Distillation of the residue provided the desired compound (1a) as a clear colorless oil; bp 126°-136° C. (15 mm); NMR 4.38 (2 H, s), 6.6-7.7 (3 H, m).

Workup

  1. temperatureRefluxing
  2. customirradiation
  3. concentrationthe clear pale amber solution was concentrated
  4. distillationDistillation of the residue

Sources & evidence

ORD record
ord-7906c46b5bd04dc88f63fabee62f96e3
Source dataset
uspto-grants-1988_09
Patent number
US04772626

Reaction notes

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