Benzoyl Peroxide → 4-Cyano-3-fluorobenzyl bromide

HRID 1835675Notes

Reaction equation

HRID 1835675 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 27784664-Cyano-3-fluorobenzyl bromideYield 56.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-fluoro-4-methylbenzonitrile (1 g, 7.4 mmol), benzoylperoxide (0.39 g, 1.6 mmol), and N-bromosuccinimide (1.9 g, 10.6 mmol) in carbontetrachloride (100 mL) was heated at reflux for 3 h. The resulting suspension was filtered and the filtrate diluted with dichloromethane, washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:n-hexane, 1:9) to give the title compound as a yellow oil (0.9 g, 56%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe resulting suspension was filtered
  4. additionthe filtrate diluted with dichloromethane
  5. washwashed with a saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (EtOAc:n-hexane, 1:9)

Sources & evidence

ORD record
ord-2978e4296793448482f120c1180a8983
Source dataset
uspto-grants-2004_08
Patent number
US06774110B2

Reaction notes

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