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

HRID 1408785
Notes
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Reaction equation

HRID 1408785 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-ddb9009919f845a1a9c80b2f516fc88c
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921359B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes