Ethanol → HCID 58423772, compound

HRID 1408649Notes

Reaction equation

HRID 1408649 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.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.CCO>O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:17]([C:16]1[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=1)[CH2:9][C:8]2=[O:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 77264-ChlorobenzaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58423772HCID 58423772, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (6 g, 28 mmol), 4-chloro-benzaldehyde (3.92 g, 28 mmol), and borax (10H2O, 10.67 g, 28 mmol) in H2O (60 mL) and EtOH (36 mL) was stirred at 110° C. overnight. The mixture was filtered to give a solid cake. The cake was dissolved in EtOAc and filtered. The filtrate was dried, filtered, and concentrated to give 6-bromo-2-(4-chloro-phenyl)-chroman-4-one (8.43 g, 89%). 1H-NMR (CDCl3): 2.88 (m, 1H), 3.04 (m, 1H), 5.44 (m, 1H), 6.94 (m, 1H), 7.39 (m, 4H), 7.57 (m, 1H), 8.02 (m, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customto give a solid cake
  3. filtrationfiltered
  4. customThe filtrate was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-06e081d59eac46d89bf822a9a08d07c0
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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