Benzoyl Peroxide → 3-(Bromomethyl)-4-fluorobenzonitrile

HRID 1360678Notes

Reaction equation

HRID 1360678 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[C:6]#[N:7]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27791804-Fluoro-3-methylbenzonitrile

Product 1

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrileYield 74.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-fluoro-3-methylbenzonitrile (15.0 g, 111 mmol), in CCl4 (600 mL) was added N-bromosuccinimide (23.7 g, 133 mmol), and benzoyl peroxide (5.38 g, 22.2 mol). The mixture was irradiated with a sunlamp (250 W) to create a gentle reflux. After 0.5 hours of exposure the reaction was complete by TLC. The reaction mixture was cooled and filtered through celite. The filtrate was condensed in vacou to yield brown oil. The crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate) to yield 17.7 g of the desired product.

Workup

  1. customThe mixture was irradiated with a sunlamp (250 W)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. customcondensed in vacou
  5. customto yield brown oil
  6. customThe crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e08561509d4340ada56c3f86cd87b461
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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