2-Chloro-6-nitrobenzaldehyde → 2-(2-Chloro-6-nitrophenyl)-2-((trimethylsilyl)oxy)acetonitrile

HRID 2202667Notes

Reaction equation

HRID 2202667 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=[O:5].[Si:13](C#N)([CH3:16])([CH3:15])[CH3:14].[CH3:19][N+:20]1([O-])CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]([O:5][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:19]#[N:20]

Participants

5

Reactant 3

HCID 807012-Chloro-6-nitrobenzaldehydeHCID 82029Methyl morpholine oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 1317357672-(2-Chloro-6-nitrophenyl)-2-((trimethylsilyl)oxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-6-nitrobenzaldehyde (1.0 g, 5.4 mmol) in DCM (15 mL) were added TMSCN (1.0 mL, 8.1 mmol) and NMO (0.19 g, 1.6 mmol) at room temperature and stirred for 1 h. The reaction mixture was quenched with water (50 mL) and extracted with DCM (2×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to get compound A84-1 (1.0 g, 67%) as a brown color oil.

Workup

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with DCM (2×30 mL)
  3. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto get compound A84-1 (1.0 g, 67%) as a brown color oil

Sources & evidence

ORD record
ord-e94cf7051ba84b05aa83aeda2365200b
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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