Dimethylformamide → 3-Bromo-2-methylbenzonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](F)[CH:9]=1)[C:5]#[N:6].Br[C:12]1C=CC=C(Br)C=1C.CN(C=O)C.[Cu]C#N>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35%) of 3-bromo-2-methylbenzonitrile. Data for 3-bromo-2-methylbenzonitrile: 1H NMR (400 MHz, acetone-d6) 7.88 (d, J=8.0, 1H), 7.73 (d, J=8.0, 1H), 7.32 (t, J=15.8, 7.9, 1H), 2.58 (s, 3H).
Workup
- customThis compound was prepared in a manner similar to
- customThe crude product was purified by flash column chromatography (100 mL silica, hexane)
Sources & evidence
- ORD record
- ord-8a74568bc0f04567ba9a5cf128124c7f
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448405B1
Reaction notes
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