o-Fluorobenzaldehyde → 6-Bromo-2-(2-fluorophenyl)chroman-4-one

HRID 2096477Notes

Reaction equation

HRID 2096477 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:15]([C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[F:12])[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 584240876-Bromo-2-(2-fluorophenyl)chroman-4-oneYield 66.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (15 g, 70.1 mmol), 2-fluorobenzaldehyde (8.7 g, 70.1 mmol), and borax (26.7 g, 70.1 mmol) in ethanol (90 mL) and H2O (150 mL) was refluxed for one day. The reaction mixture was cooled, diluted with an equal volume of H2O, and extracted with ether. The ether was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-2-(2-fluorophenyl)chroman-4-one (15 g, 50%).

Workup

  1. temperaturewas refluxed for one day
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. dry with materialThe ether was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e8d40ce73f8046d0996bf843ba1bed2f
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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