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

HRID 1503383Notes

Reaction equation

HRID 1503383 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 (2.1385 g, 10.53 mmol) and DMAP (0.0146 g, 0.12 mmol, 0.011 equiv) in CH3CN (20 mL) was added TMSCN (1.4086 g, 14.20 mmol, 1.35 equiv) dropwise via a syringe under nitrogen at room temperature. After 4 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-b783233118a349c6bb8fa3ed008d4f20
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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