5'-Bromo-2'-hydroxyacetophenone → HCID 58424670, compound

HRID 1408693Notes

Reaction equation

HRID 1408693 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.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]=O)[CH2:14][CH2:13]1>CCO.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:18]([CH:15]1[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 58424670HCID 58424670, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (943.9 mg, 4.39 mmol) in EtOH (5.6 mL) and H2O (9.4 mL) was added tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 4.39 mmol) and borax (1.67 g, 4.39 mmol). The mixture was refluxed overnight. Then the mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was dissolved in CH2Cl2 and filtrated. The filtrate was concentrated in vacuo to give the crude product, which was purified by column chromatography to give 6-bromo-2-(tetrahydro-2H-pyran-4-yl)chroman-4-one (270 mg, 20%). 1H-NMR (CDCl3, 400 MHz): 1.54 (m, 2H), 1.78 (m, 1H), 1.95 (m, 1H), 2.75 (m, 2H), 3.44 (m, 3H), 4.09 (m, 2H), 4.15 (m, 1H), 6.89 (m, 1H), 7.56 (m, 1H), 8.01 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThen the mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in CH2Cl2
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7be01d01f1694dbfa8192435683322b3
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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