Acetonitrile → 2-(5-Bromo-2-fluorophenyl)-2-((trimethylsilyl)oxy)acetonitrile

HRID 473000Notes

Reaction equation

HRID 473000 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Si:11](C#N)([CH3:14])([CH3:13])[CH3:12].C[C:18]#[N:19]>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]([O:8][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:18]#[N:19])[CH:9]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 581975642-(5-Bromo-2-fluorophenyl)-2-((trimethylsilyl)oxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (3.4160 g, 16.8 mmol) and DMAP (0.0256 g, 0.21 mmol, 0.012 equiv) in CH3CN (35 mL) was added TMSCN (1.8885 g, 19.0 mmol, 1.13 equiv) dropwise via a syringe under nitrogen at room temperature. After 3.75 h, the solvent was removed under reduced pressure. The crude product was directly used in the next step without further purification.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude product was directly used in the next step without further purification

Sources & evidence

ORD record
ord-d8ac01e372d44d6f81bd9369792dc4f9
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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