5-Bromo-2-iodobenzonitrile → 5-Bromo-2-isobutylbenzonitrile

HRID 1821015Notes

Reaction equation

HRID 1821015 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[C:7]#[N:8].[Br-].[CH2:12]([Zn+])[CH:13]([CH3:15])[CH3:14]>>[CH3:12][CH:13]([CH3:15])[CH2:14][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

3

Reactant 2

HCID 70208745-Bromo-2-iodobenzonitrileHCID 178448254HCID 178448254, compound

Product 1

HCID 513581655-Bromo-2-isobutylbenzonitrile

Procedure

5-Bromo-2-iodobenzonitrile (3.25 mmol) was combined with 6.5 mL of 0.5 M solution of iso-butylzinc bromide, the solution was degassed with argon, 100 mg of tetrakis(triphenylphosphine) palladium was added in one portion and the solution was stirred at rt under argon for 48 h. The solvents were removed under reduced pressure and the residual mixture was purified by column chromatography using Biotage 40L cartridge to obtain the title compound: 1H NMR (500 MHZ, CDCl3) δ 0.97 (d, J=8.5, 6H), 2.00 (m, 1H), 2.71 (d, J=7.5, 2H), 7.19 (d, J=8.5, 1H), 7.65 (dd, J=8.5, 2.0, 1H), 7.76 (d, J=2.0, 1H).

Workup

  1. customthe solution was degassed with argon, 100 mg of tetrakis(triphenylphosphine) palladium
  2. additionwas added in one portion
  3. customThe solvents were removed under reduced pressure
  4. customthe residual mixture was purified by column chromatography

Sources & evidence

ORD record
ord-48bd4873eeea42bcafc5910beee6c883
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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