Sodium Hydroxide → HCID 58424383, compound

HRID 2096531Notes

Reaction equation

HRID 2096531 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-cabc50bdc08d4b37a8bda15b89a4ad84
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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