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

HRID 1503418Notes

Reaction equation

HRID 1503418 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-d5f54fbf1a014a22a0d2afa5e8c4cadd
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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