Water → 2-(7-Chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile

HRID 705703Notes

Reaction equation

HRID 705703 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([CH2:11]Cl)[CH:3]=1.[C-:13]#[N:14].[Na+].O>CS(C)=O>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([CH2:11][C:13]#[N:14])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 162270934-Chloro-6-(chloromethyl)-1,3-dioxaindane

Product 1

HCID 670440102-(7-Chlorobenzo[d][1,3]dioxol-5-yl)acetonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-chloro-6-(chloromethyl)-1,3-benzodioxole (30.0 g, 0.147 mol) and NaCN (7.94 g, 0.162 mol) in DMSO (80 mL) was stirred at 40° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (3×130 mL). The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure to afford the title compound (14.2 g; 50%).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×130 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-15eb51b82bcf41a9b20d5766c331db7a
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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