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

HRID 2420253Notes

Reaction equation

HRID 2420253 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11]Br)=[CH:10][C:4]=2[O:3]1.[C-:14]#[N:15].[K+].[Br-].[K+]>O>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][C:14]#[N:15])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 253877Potassium BromideHCID 203113835-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

Product 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,2-difluoro-5-bromomethyl-1,3-benzodioxole (41.0 g) in absolute alcohol (160 ml) at 60° to 70° C a hot solution of potassium cyanide (22.1 g, 0.34 mole) in water (30 ml) is added. There is a slight exotherm and within 5 minutes potassium bromide separates out of the reaction mixture. The reaction mixture is refluxed for 1.5 hours, cooled and added to ice-water. The mixture is extracted with ether (3×100 ml), the combined extracts are washed with water (2×50 ml), dried over sodium sulfate and evaporated to afford a dark oil. Vacuum distillation yields 21.2 g of title product; b.p. 64° to 67° C (at 0.03 mm); i.r. (neat) 2255 cm-1 ; nmr (CCl4) δ 3.68 (S, 2H), 7.00 (S, 3H).

Workup

  1. temperatureThe reaction mixture is refluxed for 1.5 hours
  2. temperaturecooled
  3. extractionThe mixture is extracted with ether (3×100 ml)
  4. washthe combined extracts are washed with water (2×50 ml)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto afford a dark oil
  8. distillationVacuum distillation

Sources & evidence

ORD record
ord-70e7b5af9f1a4bea9c025c804f6cbfb9
Source dataset
uspto-grants-1978_08
Patent number
US04110345

Reaction notes

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