4-Bromophenol → 2-(4-Bromophenoxy)pyridine

HRID 84248

Reaction equation

HRID 84248 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[OH-].[Na+]>CN1CCCC1=O.[Cu].[Cu]I>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 78084-BromophenolHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 232019352-(4-Bromophenoxy)pyridineYield 76%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of copper powder (6.4 mg, 0.1 mmol, 0.1 equiv), copper (I) iodide (19 mg, 0.1 mmol, 0.1 equiv), potassium carbonate (484 mg, 3.5 mmol, 3.5 equiv), 4-bromophenol (190 mg, 1.1 mmol, 1.1 equiv), and 2-bromopyridine (158 mg, 1.0 mmol, 1.0 equiv) in 1-methyl-2-pyrrolidinone (1.0 mL) was heated to 140° C. for 5 days. A solution of 1 M sodium hydroxide (15 mL) was added, and the mixture was extracted with ethyl acetate (1×30 mL). The organic phase was washed with 1 M sodium hydroxide (15 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography (30% ethyl acetate in heptane) to provide a colorless oil (190 mg, 76%). MS (LCMS) m/z 250.4 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (1×30 mL)
  2. washThe organic phase was washed with 1 M sodium hydroxide (15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography (30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-e32d932da2d54074abc696d7be9e38eb
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Linked notes

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