N-bromobutanimide → 4-Bromomethyl-2-fluoropyridine

HRID 256171

Reaction equation

HRID 256171 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 139851684-Bromomethyl-2-fluoropyridineYield 24.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

By the method of Example 20, 10 g (0.09 mole) of 2-fluoro-4-methylpyridine and 16 g (0.09 mole) of N-bromosuccinimide were reacted in 90 ml of carbon tetrachloride to produce 4.18 g 4-bromomethyl-2-fluoropyridine. The ir, proton nmr, and 19F nmr spectra were all consistent with the proposed structure.

Sources & evidence

ORD record
ord-34c5140a392d4dbeb1659ba46ee7b0da
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Linked notes

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