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

HRID 1408578Notes

Reaction equation

HRID 1408578 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%). 1HNMR (CDCl3): 2.8 (d, 1H), 3.0 (t, 1H), 5.7 (d, 1H), 6.7 (d, 1H), 6.9 (t, 1H), 7.2 (m, 2H), 7.3 (m, 2H), 7.5 (m, 2H), 7.9 (t, 1H), 8.1 (d, 1H).

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-2ddbc606791b4bff97ad5d5b1048ef0d
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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