Benzoyl Peroxide → N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide

HRID 226919Notes

Reaction equation

HRID 226919 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:4].CC1N=C(N)C=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:36]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:12][C:8]1[N:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:13])[F:14])[CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 7187Benzoyl PeroxideHCID 9845Trifluoroacetic anhydrideHCID 157652-Amino-6-methylpyridineHCID 67184N-bromobutanimideHCID 36439582,2,2-trifluoro-N-(6-methylpyridin-2-yl)acetamide2×

Product 1

HCID 57754672N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

2,2,2-trifluoro-N-(6-methyl-pyridin-2-yl)-acetamide xxii can be prepared from 6-methyl-pyridin-2-ylamine and trifluoroacetic anhydride in DCM. Radical bromination of xxii with N-bromosuccinimide and benzoyl peroxide in refluxing carbon tetrachloride affords N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide xxiii.

Sources & evidence

ORD record
ord-9cbcaa9802c84d30917a5b15fc2551e1
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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