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

HRID 17942

Reaction equation

HRID 17942 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([F:13])([F:12])[O:9]C(F)(F)[C:7]=2[CH:16]=1.[C-:17]#[N:18].[Na+]>CS(C)=O>[F:13][C:10]1([F:12])[O:11][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][C:17]#[N:18])=[CH:16][C:7]=2[O:9]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 591658634H-1,3-Benzodioxin, 6-(chloromethyl)-2,2,4,4-tetrafluoro-

Product 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileYield 94.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6-chloromethyl-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine (6.2 g) and NaCN (2.07 g, 42.3 mmol) in DMSO (50 mL) was stirred at room temperature for 2 h. The reaction mixture was poured into ice and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to give a crude product, which was purified by silica gel column (Petroleum Ether/EtOAc 10:1) to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile (4.5 g, 68% over 3 steps). 1H NMR (CDCl3, 300 MHz) δ 7.57-7.60 (m, 2H), 7.20 (d, J=8.7 Hz, 1H), 3.82 (s, 2H).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated
  5. customto give a crude product, which
  6. customwas purified by silica gel column (Petroleum Ether/EtOAc 10:1)

Sources & evidence

ORD record
ord-e30f4bd447bb4d8ab94992bc8516ec0c
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Linked notes

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