Hydrochloric Acid → HCID 58423873, compound

HRID 2096530Notes

Reaction equation

HRID 2096530 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.[F:12][C:13]([F:24])([F:23])[O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[OH-].[Na+].Cl>CCO.O.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])/[CH:9]=[CH:19]/[C:18]2[CH:21]=[CH:22][C:15]([O:14][C:13]([F:12])([F:23])[F:24])=[CH:16][CH:17]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58423873HCID 58423873, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (20 g, 93.4 mmol) in EtOH (114 mL) and H2O (6 mL) was added 4-(trifluoromethoxy)benzaldehyde (17.75 g, 93.4 mmol) and NaOH (33.6 g, 840.6 mmol). The reaction mixture was stirred overnight. Ethoxyethane was added to the mixture and filtered to give a residue. The residue was dissolved in water and acidified by 1 M HCl to give a solid. The solid was collected by filtration to give (E)-1-(5-bromo-2-hydroxyphenyl)-3-(4-(trifluoromethoxy)phenyl)prop-2-en-1-one (30 g, 80%). 1H-NMR (CDCl3): 6.87 (d, 1H), 7.21 (d, 2H), 7.49 (m, 1H), 7.52 (m, 1H), 7.59 (d, 2H), 7.84 (t, 1H), 7.92 (s, 1H).

Workup

  1. filtrationfiltered
  2. customto give a residue
  3. customto give a solid
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-b7b841d9579a49a09532c78f23b273f1
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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