2,5-Dibromopyridine → 2-[4-(5-Bromopyridin-2-ylethynyl)phenoxy]ethanol

HRID 734795Notes

Reaction equation

HRID 734795 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[CH:5][CH:4]=1)#[CH:2].Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1>CCOC(C)=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:2]#[C:1][C:3]2[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[CH:5][CH:4]=2)=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 693532,5-DibromopyridineHCID 187514152-(4-Ethynylphenoxy)ethan-1-ol

Product 1

HCID 690603712-[4-(5-Bromopyridin-2-ylethynyl)phenoxy]ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product was obtained analogously to Example 1.1d starting from 7.70 g (47.48 mmol) of 2-(4-ethynylphenoxy)ethanol and 11.37 g (48.00 mmol) of 2,5-dibromopyridine. Yield: 7.40 g (49% of theoretical); C15H12BrNO2 (M=318.165); calc.: molpeak (M+H)+: 318/320 (Br); found: molpeak (M+H)+: 318/320 (Br); Rf value: 0.20 (silica gel, PE/EtOAc 6:4).

Workup

  1. customThe product was obtained analogously to Example 1.1d

Sources & evidence

ORD record
ord-3f2a23d8988d4ff2af1bb25f218aabd2
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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