Nitrogen → 2-(Bromomethyl)-5-fluorobenzonitrile

HRID 1664156Notes

Reaction equation

HRID 1664156 reaction equation
N#N.[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:12])=[C:8]([CH:11]=1)[C:9]#[N:10].C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:11][C:8]=1[C:9]#[N:10]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5226685-Fluoro-2-methylbenzonitrile

Product 1

HCID 220157702-(Bromomethyl)-5-fluorobenzonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N2 was passed through a mixture of 5-fluoro-2-methylbenzonitrile (28.51 g, 211 mmol), NBS (41.31 g, 232 mmol) and AIBN (2.5 g, 15 mmol) in CCl4 (845 mL) for 10 min after which the reaction was heated at reflux for 8 h. After standing at room temperature overnight, the reaction mixture was filtered and the filter cake washed with CCl4 (500 mL). The combined filtrate was evaporated to give a yellow oil. Flash chromatography (SiO2) using 5-25% ethyl acetate/Hexanes as eluent afforded the title compound (29.74 g, 66% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) &: 7.55 (1H, dd, J=8.6, 5.2 Hz), 7.37 (1H, dd, J=7.9, 2.8 Hz), 7.32-7.28 (1H, m), 4.61 (2H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. filtrationthe reaction mixture was filtered
  4. washthe filter cake washed with CCl4 (500 mL)
  5. customThe combined filtrate was evaporated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-0598a45bb42e4ebdb9652883a1f4b083
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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