Sodium Hydroxide → HCID 58424383, compound

HRID 1408719Notes

Reaction equation

HRID 1408719 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([C:8](=[O:22])/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CCO.O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:23][CH:10]([C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:15][CH:16]=1)[CH2:9][C:8]2=[O:22]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58423873HCID 58423873, compound

Product 1

HCID 58424383HCID 58424383, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(4-(trifluoromethoxy)phenyl)prop-2-en-1-one (8 g, 20 mmol) in EtOH (144 mL) and H2O (432 mL) was added NaOH (800 mg, 20 mmol). The reaction mixture was stirred overnight. The mixture was filtered to give a solid residue. The solid residue was dissolved in EtOAc. The resulting solution was dried over Na2SO4 and then concentrated in vacuo to give 6-bromo-2-(4-(trifluoromethoxy)phenyl)chroman-4-one (6 g, 80%). 1H-NMR (CDCl3): 2.91 (d, 1H), 3.04 (m, 1H), 5.49 (dd, 1H), 6.94 (m, 1H), 7.31 (d, 2H), 7.50 (d, 2H), 7.59 (m, 1H), 8.03 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customto give a solid residue
  3. dry with materialThe resulting solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e12041d9f3fd42a49c393741adb6995e
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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