Water → Benzo-1,3-dioxole-5-carbonitrile

HRID 538606

Reaction equation

HRID 538606 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].Br[CH2:12]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[O:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[O:1][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 870653,4-Dihydroxybenzonitrile

Product 1

HCID 78136Benzo-1,3-dioxole-5-carbonitrileYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3,4 Dihydroxy benzonitrile (5.0 g, 37.0 mmol) in 20 ml of DMF was added dibromomethane (19.25 g, 110.0 mmol) and potassium carbonate (25.50 g, 184.90 mmol). The reaction mixture was heated at 120° C. for 2 h under the nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), reaction mixture was cooled to room temperature. Water (50 ml) was added to the reaction mixture and extracted the compound with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure to give the title compound as yellow solid (5.16 g, 94.8%).

Workup

  1. customAfter the completion of the reaction mixture (TLC monitoring), reaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted the compound with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-dac97f44beb24917a37737a85db83b1b
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Linked notes

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