3-Fluorobenzaldehyde → 6-Bromo-2-(3-fluorophenyl)chroman-4-one

HRID 2096439Notes

Reaction equation

HRID 2096439 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:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=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:16]([C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 584240686-Bromo-2-(3-fluorophenyl)chroman-4-oneYield 36.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (15 g, 0.07 mol), 3-fluorobenzaldehyde (8.7 g, 0.07 mol) and borax (26.7 g, 0.07 mol) 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 ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-2-(3-fluorophenyl)chroman-4-one (8.3 g, 3.7%). 1H-NMR (CDCl3): 2.93 (d, 1H), 3.03 (m, 1H), 5.47 (d, 1H), 7.06 (d, 1H), 7.11 (m, 1H), 7.22 (m, 2H), 7.40 (m, 1H), 7.57 (d, 1H), 8.04 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-0ee9580a85144962ad224a91ccd30e8e
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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