Potassium Carbonate → 3-Bromo-2-(cyclopropylmethoxy)benzaldehyde

HRID 523995Notes

Reaction equation

HRID 523995 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.[C:16]([O-:19])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:6][CH:7]=[C:8]([C:16]=1[O:19][CH2:12][CH:13]1[CH2:15][CH2:14]1)[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 37146742-Bromo-3-hydroxybenzaldehyde

Product 1

HCID 597250443-Bromo-2-(cyclopropylmethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

300 mg (1.49 mmol) 2-Bromo-3-hydroxy-benzaldehyde, 302 mg (2.24 mmol) (bromomethyl)cyclopropane and 412 mg (2.99 mmol) K2CO3 in 3 mL DMF are stirred at 80° C. over night. Afterwards the reaction mixture is diluted with water and extracted with EtOAc. The organic layer is separated and dried over Na2SO4, filtered and the solvent is removed in vacuo.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer is separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1ee4c086c6534256b2b3745d812ea9f3
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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