Water → HCID 117926708, compound

HRID 590625Notes

Reaction equation

HRID 590625 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11]Br.O.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:11][CH2:10][Br:9])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 117926708HCID 117926708, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-3-hydroxypyridine (2 g, 11.56 mmol) was dissolved in anhydrous DMF (20 mL); to which 1,2-dibromoethane (10 g, 57.82 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, water (100 mL) was added to it and extraction was carried out using EtOAc (30 mL×3). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified using silica gel column chromatography to provide Q-1-I (2.7 g, 86% yield). LCMS: m/z; 280.0 (M+1)+.

Workup

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. customto provide Q-1-I (2.7 g, 86% yield)

Sources & evidence

ORD record
ord-a5367032fa624ee19cd5a4d5d5e5f3b9
Source dataset
uspto-grants-2016_01
Patent number
US09233983B2

Reaction notes

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