Sodium Cyanide → 2,5-Dichloro-3-methoxyphenylacetonitrile

HRID 274841Notes

Reaction equation

HRID 274841 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Cl:10])=[CH:4][C:3]=1[CH2:11]Br.[C-:13]#[N:14].[Na+]>O.CO>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Cl:10])=[CH:4][C:3]=1[CH2:11][C:13]#[N:14]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 214781051-(Bromomethyl)-2,5-dichloro-3-methoxybenzene

Product 1

HCID 543521902,5-Dichloro-3-methoxyphenylacetonitrileYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

By the method of Example 1, Step C, 15.40 grams (0.057 mole) of 2,5-dichloro-3-methoxyphenylmethyl bromide and 3.63 grams (0.074 mole ) of sodium cyanide were reacted in 70 mL of water and 65 mL of methanol, yielding 12.0 g of 2,5-dichloro-3-methoxyphenylacetonitrile as an oil that solidified on standing, m.p. 53°-57° C. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-17cb2a5faee44c58b3165e817791a110
Source dataset
uspto-grants-1995_02
Patent number
US05391541

Reaction notes

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