2-Thiophenecarboxaldehyde → HCID 10709982, compound

HRID 2096387Notes

Reaction equation

HRID 2096387 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.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=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:17]([C:13]1[S:12][CH:16]=[CH:15][CH:14]=1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 10709982HCID 10709982, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (20 g, 0.093 mol), thiophene-2-carbaldehyde (10.46 g, 0.093 mol) and borax (35.4 g, 0.093 mol) in ethanol (120 mL) and H2O (200 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-thiophen-2-yl-chroman-4-one (16 g, 50%). 1H-NMR (CDCl3): 3.01 (m, 1H), 3.10 (m, 1H), 5.75 (dd, 1H), 6.94 (d, 1H), 7.02 (t, 1H), 7.05 (d, 1H), 7.32 (d, 1H), 7.54 (dd, 1H), 8.00 (d, 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-f9d927cc53dc4126bd68c66a77255069
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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