Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-5-chloro-2-fluorobenzene

HRID 508412Notes

Reaction equation

HRID 508412 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[C:4]([Cl:10])[CH:3]=1.[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([CH2:9][Br:11])=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27362284-Bromo-2-chloro-5-fluorotoluene

Product 1

HCID 666667551-Bromo-4-(bromomethyl)-5-chloro-2-fluorobenzene

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8900HeptaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 4-bromo-2-chloro-5-fluorotoluene (997 mg, 4.46 mmol), N-bromosuccinimide (837 mg, 4.70 mmol) and benzoyl peroxide (35 mg, 0.14 mmol) in carbon tetrachloride (20 mL) was heated to reflux at 85° C. for 18.5 hours under nitrogen. The reaction mixture was concentrated in vacuo to afford a cream solid residue. The residue was suspended in heptane (40 mL), filtered and the filtrate then concentrated in vacuo to afford the title compound a clear oil (1.35 g, 100%). The compound was used without further purification in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto afford a cream solid residue
  3. filtrationfiltered
  4. concentrationthe filtrate then concentrated in vacuo

Sources & evidence

ORD record
ord-0527604248cb4cef927ba5efaab48d78
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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