Potassium Carbonate → HCID 59581200, compound

HRID 1754062Notes

Reaction equation

HRID 1754062 reaction equation
Br[C:2]1[C:11]([Br:12])=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[C:13]([Cu])#[N:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:12][C:11]1[C:2]([C:13]#[N:14])=[CH:3][C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27545026,7-DIBROMOBENZO(1,4)DIOXANHCID 178418546HCID 178418546, compound

Product 1

HCID 59581200HCID 59581200, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 20.0 g (62.6 mmol) of 6,7-dibromo-2,3-dihydrobenzo[1,4]dioxine, 8.50 g (93.9 mmol) CuCN and 13.0 (93.9 mmol) K2CO3 in 300 mL DMF is stirred at 150° C. for 6 d. The reaction is quenched by the addition of water and extracted with EtOAc. The org. layers are combined and washed with water (3×) and sat. aq. NaCl solution. After drying over Na2SO4, the mixture is filtered and the solvent is removed in vacuo. The resulting residue is purified by column chromatography (silica gel, PE/EtOAc 20/1→10/1).

Workup

  1. customThe reaction is quenched by the addition of water
  2. extractionextracted with EtOAc
  3. washwashed with water (3×) and sat. aq. NaCl solution
  4. dry with materialAfter drying over Na2SO4
  5. filtrationthe mixture is filtered
  6. customthe solvent is removed in vacuo
  7. customThe resulting residue is purified by column chromatography (silica gel, PE/EtOAc 20/1→10/1)

Sources & evidence

ORD record
ord-d7fc5e04cc1e429bb5396ec9eaa4d9b7
Source dataset
uspto-grants-2015_10
Patent number
US09169205B2

Reaction notes

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