Water → 2-[(1,1-Dimethylethyl)oxy]-6-chlorobenzonitrile

HRID 374958

Reaction equation

HRID 374958 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+].O>COCCOC>[CH3:11][C:12]([O:14][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 695872-Chloro-6-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 189963822-[(1,1-Dimethylethyl)oxy]-6-chlorobenzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-fluoro-6-chlorobenzonitrile (10.35 g, 66.5 mmol) in 1,2-dimethoxyethane (50 mL) at 0° C. was added potassium t-butoxide (9.06 g, 80.7 mmol). The mixture was slowly allowed to warm to room temperature over 3 h. The reaction was poured into water and extracted with ether (3 times). The organic layers were washed with brine, dried (MgSO4) and concentrated to afford 13.52 g (97%) of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzonitrile as a pale yellow oil.

Workup

  1. extractionextracted with ether (3 times)
  2. washThe organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a2e91e7ca3d4b1c9099bb9e886652b1
Source dataset
uspto-grants-1996_01
Patent number
US05482974

Linked notes

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