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Benzyl Bromide → 2-Benzyloxy-3-bromo-5-trifluoromethylpyridine

HRID 1976063
Notes
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Reaction equation

HRID 1976063 reaction equation
[Br:1][C:2]1[C:3](=[O:12])[NH:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCCCCC.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:12][C:3]1[C:2]([Br:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 134917753-Bromo-5-(trifluoromethyl)pyridin-2(1H)-one

Product 1

HCID 220001982-Benzyloxy-3-bromo-5-trifluoromethylpyridineYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8058HexaneSolvent

Procedure

3-Bromo-5-trifluoromethyl-2(1H)-pyridone (6.09 g, 25.2 mmol) and silver carbonate (7.18 g, 26.0 mmol) were suspended in hexane (200 mL) and treated with benzyl bromide (6 mL, 50.3 mmol). The mixture was stirred for 18 hrs, then filtered. The filtrate was concentrated and the residue purified by silica chromatography to give the product as a white solid (7.65 g, 23 mmol, 91% yield).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-33da332533ff41c3a8792822a9d935af
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06225320B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes