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Benzaldehyde → 1-(5-Bromo-4-fluoro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one

HRID 2096598
Notes
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Reaction equation

HRID 2096598 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH:9]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 584243681-(5-Bromo-4-fluoro-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 671755841-(5-Bromo-4-fluoro-2-hydroxyphenyl)-3-phenylprop-2-en-1-oneYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a bottle were combined 1-(5-bromo-4-fluoro-2-hydroxyphenyl)ethanone (8.63 g, 37.15 mmol), benzaldehyde (3.94 g, 37.15 mmol), EtOH (96%, 45 mL) and NaOH (13.08 g, 327 mmol). The mixture was stirred vigorously for 0.5 h. and then filtered. The mixture was poured into HCl (1 N, 50 mL) and filtered. The solid was dried to give 1-(5-bromo-4-fluoro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one (10.8 g, 91%).

Workup

  1. filtrationfiltered
  2. additionThe mixture was poured into HCl (1 N, 50 mL)
  3. filtrationfiltered
  4. customThe solid was dried

Sources & evidence

ORD record
ord-ce1a568f617b44b890d16860ed39f9c6
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450308B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes