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Hydrochloric Acid → 2-(4-Bromophenoxy)pyridine

HRID 40698
Notes
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Reaction equation

HRID 40698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 97462-FluoropyridineHCID 24758Sodium hydride

Product 1

HCID 232019352-(4-Bromophenoxy)pyridineYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

4-Bromophenol (2 g, 11.5 mmol) is placed in 10 ml of anhydrous DMF under nitrogen. Sodium hydride (0.51 g, 127 mmol) is added. After stirring for 20 min at ambient temperature, 2-fluoropyridine (1.05 ml, 12.1 mmol) is added and the reaction medium is heated at 105° C. for 7 h. After hydrolysis, the pH is adjusted to 8 with a 1N aqueous solution of HCl. The reaction medium is then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in heptane ranging from 0% to 30%. 2.22 g of expected 2-(4-bromo-phenoxy)pyridine are obtained,

Workup

  1. temperaturethe reaction medium is heated at 105° C. for 7 h
  2. customAfter hydrolysis
  3. extractionThe reaction medium is then extracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-55b4b911dcaf480b88a1b9de8397e19c
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530477B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes