Potassium Carbonate → 2-Bromo-5-cyclopropoxybenzonitrile

HRID 1754060Notes

Reaction equation

HRID 1754060 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[CH:17]1(Br)[CH2:19][CH2:18]1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH:17]2[CH2:19][CH2:18]2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78037BromocyclopropaneHCID 153231112-Bromo-5-hydroxybenzonitrile

Product 1

HCID 900921522-Bromo-5-cyclopropoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 2.50 g (13 mmol) 2-bromo-5-hydroxy-benzonitrile in 100 mL DMF are added 5.23 g (38 mmol) K2CO3 and 3.05 g (25 mmol) cyclopropylbromide. The reaction mixture is stirred for 16 h at 120° C. Afterwards the reaction is quenched by the addition of ice water and extracted with EtOAc. The org. layers are combined, washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc).

Workup

  1. customAfterwards the reaction is quenched by the addition of ice water
  2. extractionextracted with EtOAc
  3. washwashed with sat. aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc)

Sources & evidence

ORD record
ord-dcb86598e3fa4cc6b8d7b0b568b329bd
Source dataset
uspto-grants-2015_10
Patent number
US09169205B2

Reaction notes

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