Sodium Cyanide → HCID 66967418, compound

HRID 532866Notes

Reaction equation

HRID 532866 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.BrCC1C=CC=C(Cl)C=1OC.[C-]#N.[Na+]>CCO.CCOCC>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 17989277(3-Chloro-2-methoxyphenyl)acetonitrileHCID 19390097HCID 19390097, compound

Product 1

HCID 66967418HCID 66967418, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. washThe mixture was washed with H2O and brine
  3. extractionthe aq. phase was extracted again with Et2O
  4. dry with materiallayers dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-cf8f899aaa96433fa2d583162f869a5e
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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