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

HRID 640596Notes

Reaction equation

HRID 640596 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 59.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-chloro-6-(chloromethyl)benzo[d][1,3]dioxole (6.0 g, 29 mmol) and NaCN (1.6 g, 32 mmol) in DMSO (20 mL) was stirred at 40° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure to afford 2-(7-chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile (3.4 g, 58%). 1H NMR δ 6.81 (s, 1H), 6.71 (s, 1H), 6.07 (s, 2H), 3.64 (s, 2H). 13C-NMR 6149.2, 144.3, 124.4, 122.0, 117.4, 114.3, 107.0, 102.3, 23.1.

Workup

  1. extractionThe mixture was extracted with EtOAc (30 mL×3)
  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-832b08d20bd941838cf104b870bbd0a6
Source dataset
uspto-grants-2010_04
Patent number
US07691902B2

Reaction notes

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