4-Bromophenol → HCID 24705025, compound

HRID 226261Notes

Reaction equation

HRID 226261 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[C:16](=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 10176127Pyridinium chloride

Product 1

HCID 24705025HCID 24705025, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 12.75 g (77.73 mmol) of 3-chloromethyl)pyridine hydrochloride, 13.45 g (77.73 mmol) of 4-bromophenol and 27.6 g (200 mmol) of potassium carbonate in 100 ml of methyl ethyl ketone is stirred at room temperature for 24 hr and at 60° C. for 4 hr. The solids are filtered and the filtrate is concentrated. The residue is partitioned between water and diethyl ether. The ethereal layer is washed with 2N NaOH and water, and is dried and concentrated. The resulting oil (12.9 g, 49% yield) solidifies on cooling.

Workup

  1. filtrationThe solids are filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue is partitioned between water and diethyl ether
  4. washThe ethereal layer is washed with 2N NaOH and water
  5. customis dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdb5bee1a1cb43ab90e1dbbb4dccee42
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Reaction notes

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