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

HRID 1355609Notes

Reaction equation

C1C(=O)N([Br:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[F:27][C:28]1[CH:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][C:29]=1[CH3:36]>C(Cl)(Cl)(Cl)Cl.CCOCC>[F:27][C:28]1[CH:33]=[C:32]([CH:31]=[CH:30][C:29]=1[CH2:36][Br:8])[C:34]#[N:35]

Participants

Conditions

Temperature: 80 °C

Procedure

NBS (Aldrich, 3.02 g, 17 mmol) and benzoylperoxide (Aldrich, 0.37 g, 1.5 mmol) was added to a solution of 2-fluoro-4-cyanotoluene (compound 5-2, 2.08 g, 15 mmol) in CCl4. The reaction mixture was heated at 80° C. for 14 hours. After cooling down to ambient temperature, the mixture was diluted with ether (100 ml) and washed with aqueous Na2S3O3, and dried (MgSO4). Removal of solvent under vacuum led to a yellow oil which was purified by flash chromatography. The title compound 5-3 (1.4 g, 42%) was obtained, together with a by-product, 3-fluoro-4-(bromomethyl)benzonitrile (5-4) (1.0 g, 30%). For the title compound (5-3): 1H NMR (CDCl3): δ 4.46 (s, 2H), 7.35 (d, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.52 (t, 1H, J=8.0 Hz). For the by-product (5-4): 1H NMR (CDCl3): δ 6.90 (s, 1H), 7.35 (d, 1H, J=8.0 Hz), 7.55 (d, 1H, J=8.0 Hz), 7.96 (t, 1H, J=8.0 Hz).

Workup

temperatureAfter cooling down to ambient temperature
washwashed with aqueous Na2S3O3
dry with materialdried (MgSO4)
customRemoval of solvent under vacuum
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-1180974bf9e74d169e845b25ca686a7d
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586405B2

Reaction notes

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