Water → 3-(Bromomethyl)-2-fluorobenzonitrile

HRID 539311Notes

Reaction equation

HRID 539311 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].O>C(#N)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:8][CH2:18][C:17]1[C:10]([F:9])=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 231603592-Fluoro-3-methylbenzonitrile

Product 1

HCID 666784653-(Bromomethyl)-2-fluorobenzonitrileYield 70.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

NBS (1.729 g, 9.71 mmol) was added to a solution of 2-fluoro-3-methylbenzonitrile (1.25 g, 9.25 mmol) in acetonitrile (25 mL). The obtained mixture was refluxed, and then benzoic peroxyanhydride (0.045 g, 0.18 mmol) was added. The reaction mixture was refluxed overnight, then cooled to r.t. and water was added. The aqueous phase was discarded and the organic phase was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography using a gradient of EtOAc in heptane as eluent to give the title compound (1.39 g, 70% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 4.75 (s, 2 H) 7.43 (t, 1 H) 7.93 (t, 2 H); MS (EI) m/z 213 M+.

Workup

  1. temperatureThe obtained mixture was refluxed
  2. temperatureThe reaction mixture was refluxed overnight
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-09034a4e7e1e4757b50e413998ec2978
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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