Hydrogen Bromide → 2-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

HRID 852310Notes

Reaction equation

HRID 852310 reaction equation
[Na].C([CH:4]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:6])#N.Br>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:4][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[O:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 5360545SodiumHCID 141952232-(4-Fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile2×

Product 1

HCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting materials are converted in a condensation reaction with the aid of metallic sodium in an alcohol, for example ethanol, into 2-cyano-2-(4-fluorophenyl)-1-(4-pyridyl)ethanone (compound 1). The cyano group is then removed by hydrolysis, for example with hydrobromic acid, and decarboxylation, giving 2-(4-fluorophenyl)-1-(4-pyridyl)ethanone (compound 2). In the next step, compound 2 is nitrosated in the 2-position using, for example, nitrites, such as sodium nitrite or isoamyl nitrite.

Sources & evidence

ORD record
ord-e22069a620fa4983af7eb589c74b0a62
Source dataset
uspto-grants-2007_08
Patent number
US07253191B2

Reaction notes

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