4-Hydroxybenzaldehyde → 4-((2-Fluorophenyl)methoxy)benzaldehyde

HRID 2264837Notes

Reaction equation

HRID 2264837 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 7027174-((2-Fluorophenyl)methoxy)benzaldehydeYield 79.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-(bromomethyl)-2-fluorobenzene (D91, 11.5 g, 60.8 mmol), 4-hydroxybenzaldehyde (5.3 g, 43.3 mmol) and K2CO3 (12.0 g, 86.8 mmol) in acetone was divided in three equal parts and heated in a microwave apparatus at 80° C. for 40 min. The mixtures were diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. The residue was purified via flash chromatography (cyclohexanes:ethyl acetate 95:5) to give the title compound (7.9 g, 79%). Rf (cyclohexanes:ethyl acetate 8:2): 0.38.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified via flash chromatography (cyclohexanes:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-49d6201b9f7144bbb7c41bd780d1c5e4
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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