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

HRID 2168313Notes

Reaction equation

HRID 2168313 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-ff3d80e6396e466494df53a16a430b87
Source dataset
uspto-grants-2015_06
Patent number
US09045500B2

Reaction notes

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