Potassium Cyanide → HCID 66891426, compound

HRID 253315Notes

Reaction equation

HRID 253315 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][CH2:11][CH2:12][O:13][CH3:14])[C:4]=1[O:15][CH2:16][CH2:17][O:18][CH3:19].[C-:20]#[N:21].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:9][C:7]1[CH:6]=[C:5]([O:10][CH2:11][CH2:12][O:13][CH3:14])[C:4]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:3]([CH2:2][C:20]#[N:21])[CH:8]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 66890160HCID 66890160, compound

Product 1

HCID 66891426HCID 66891426, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

1-(Chloromethyl)-5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene (0.31 g, 1.06 mmol) was dissolved in N,N-dimethylformamide (2 mL) followed by the addition potassium cyanide (0.10 g, 1.7 mmol), and the resulting mixture was heated at 60° C. for 18 hours. After cooling to room temperature, it was diluted with ethyl acetate (50 mL), washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (30% ethyl acetate-hexane) to provide (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.25 g, 0.88 mmol, 85% yield). 1H NMR (400 MHz, CDCl3): 6.76-6.74 (d, d, 1H), 6.66-6.63 (d, d, 1H), 4.22-4.21 (m, 2H), 4.13-4.11 (m, 2H), 3.84 (s, 2H), 3.78-3.76 (m, 2H), 3.64-3.61 (m, 2H), 3.43 (s, 3H), 3.42 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine (20 mL each)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily residue which
  7. customwas purified by flash chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bc421c7fa19141878348a8c3a64cae26
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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