Potassium Carbonate → HCID 22391279, compound

HRID 2208140Notes

Reaction equation

HRID 2208140 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 81503Bromomethylcyclopropane

Product 1

HCID 22391279HCID 22391279, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A well stirred mixture of commercially available 3-bromo-4-hydroxy-benzaldehyde (40.2 g; 220 mmol), anhydrous K2CO3 (30.4 g; 220 mmol) and commercially available bromomethyl-cyclopropane (32.4 g; 240 mmol) in dry DMF (200 mL) is heated to 60° C. over night. The reaction mixture is filtered, concentrated under reduced pressure, diluted with water and extracted with tert. BuOMe. The combined organic extracts are washed with brine, dried over Mg2SO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/AcOEt 100:0 to 85:15) to yield 47.5 g of the title compound as pale yellow oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with tert
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Mg2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is chromatographed on silica gel (cyclohexane/AcOEt 100:0 to 85:15)

Sources & evidence

ORD record
ord-b7674975600e49c7a1b6841b7594f587
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

Loading…