Sodium Cyanide → 2,2-Difluoro-1,3-benzodioxole-5-acetonitrile

HRID 1673127Notes

Reaction equation

HRID 1673127 reaction equation
Cl[CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[O:7][C:8]([F:11])([F:10])[O:9][C:5]=2[CH:4]=1.[C-:14]#[N:15].[Na+]>CS(C)=O>[F:10][C:8]1([F:11])[O:7][C:6]2[CH:12]=[CH:13][C:3]([CH2:2][C:14]#[N:15])=[CH:4][C:5]=2[O:9]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

Product 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileYield 23,214.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole (117.6 g, crude from last step) and NaCN (84 g, 1.7 mmol) in DMSO (800 mL) was stirred for 2 h at 25° C. The reaction mixture was poured into ice and extracted with EtOAc (500 mL×3). The combined organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo to give crude product which was purified by column chromatography (P.E./EtOAc 10:1) to give 2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile (77.8 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.06-7.07 (m, 3H), 3.75 (s, 2H).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with EtOAc (500 mL×3)
  3. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give crude product which
  6. customwas purified by column chromatography (P.E./EtOAc 10:1)

Sources & evidence

ORD record
ord-7a85bc7e044a41a59a1370cefd55d64e
Source dataset
uspto-grants-2011_08
Patent number
US07999113B2

Reaction notes

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