Benzoyl Peroxide → 2-(Bromomethyl)-5-fluorobenzonitrile

HRID 1866989Notes

Reaction equation

HRID 1866989 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5226685-Fluoro-2-methylbenzonitrile

Product 1

HCID 220157702-(Bromomethyl)-5-fluorobenzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-fluoro-2-methylbenzonitrile (2.0 g, 0.015 mol), NBS (3.2 g, 0.018 mol) and benzoylperoxide (0.25 g) in carbontetrachloride (25.0 ml) was heated to reflux for 6 h, under argon atmosphere. The reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (5% EtOAc in hexane) to afford 2-(Bromomethyl)-5-fluorobenzonitrile (1.9 g, 60%) as a colorless liquid: 1H NMR (CDCl3/400 MHz) δ7.59 (m) 7.58 (m, 1H), 7.38 (m, 1H), and 7.25 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h, under argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-316c0ed079ee438f9dc179509b66aa0c
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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