Dimethylformamide → 3-Bromo-2-methylbenzonitrile

HRID 2294394Notes

Reaction equation

HRID 2294394 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

HCID 6228DimethylformamideHCID 346812,6-DibromotolueneHCID 27833303-Bromo-5-fluorobenzonitrileHCID 178418546HCID 178418546, compound

Product 1

HCID 234335373-Bromo-2-methylbenzonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. customThis compound was prepared in a manner similar to
  2. customThe crude product was purified by flash column chromatography (100 mL silica, hexane)

Sources & evidence

ORD record
ord-97967f3bbf3d4572976cad8abf142822
Source dataset
uspto-grants-1997_11
Patent number
US05688808

Reaction notes

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