Potassium Carbonate → HCID 968827, compound

HRID 2218551Notes

Reaction equation

HRID 2218551 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])[CH:14]=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:19][C:18]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][C:11]=1[Cl:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 968827HCID 968827, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

0.5 M solution of 1-bromomethyl-2-fluoro-benzene (1.5 g, 8 mmol) in DMF was added dropwise to a suspension of 3-chloro-4-hydroxy-benzaldehyde (1.14 g, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (120 mg, 0.73 mmol) in DMF (100 ml). The reaction mixture was stirred at 90° C. overnight. After cooling, the solid residue was filtered off and the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and the organic layer washed twice with NaOH 1M, dried over Na2SO4 and evaporated to dryness. The residue was purified on silica gel, obtaining 1.91 g of the title compound, yield 100%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid residue was filtered off
  3. customthe solvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer washed twice with NaOH 1M
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-277ee08477a746ab88e7c3abf2015029
Source dataset
uspto-grants-2008_08
Patent number
US07411091B2

Reaction notes

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