Potassium Carbonate → 2-[(3-Bromophenoxy)methyl]pyridine

HRID 1061805Notes

Reaction equation

HRID 1061805 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 222852832-[(3-Bromophenoxy)methyl]pyridineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromophenol (1.00 g, 5.8 mmol), 2-picolyl chloride hydrochloride (950 mg, 5.8 mmol) and potassium carbonate (3.20 g, 23 mmol) were stirred together in DMF (10 mL) at room temperature overnight. The solvent was removed in vacuo, azeotroping with xylene to remove the last traces of DMF. The residual material was partitioned between ethyl acetate (70 mL) and water (70 mL), then the organic phase was washed with saturated sodium chloride solution (1×50 mL), was dried over magnesium sulfate, and was concentrated in vacuo to afford 2-(3-bromophenoxymethyl)pyridine (1.48 g, 97%). m/z (ES+) 265 [MH]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customazeotroping with xylene
  3. customto remove the last traces of DMF
  4. customThe residual material was partitioned between ethyl acetate (70 mL) and water (70 mL)
  5. washthe organic phase was washed with saturated sodium chloride solution (1×50 mL)
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-48a0ce49428b464f854f8657309d5f33
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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