Benzoyl Peroxide → 6-Bromomethyl-nicotinic acid methyl ester

HRID 1013473Notes

Reaction equation

HRID 1013473 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 127522376-Bromomethyl-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 6-methylnicotinate (2.00 g, 13.2 mmol) and CCl4 (88.2 mL) was treated with NBS (2.57 g, 14.5 μmmol) and benzoyl peroxide (320 mg, 1.32 mmol) and heated to a refluxing temperature overnight. The resulting brown suspension was concentrated and purified by MPLC (10-40% EtOAc in heptane to afford the requisite product as a yellow solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.01 (dd, J=2.4, 0.8 Hz, 1H), 8.28 (dd, J=7.9, 2.1 Hz, 1H), 7.68 (dd, J=8.2, 0.9 Hz, 1H), 4.74 (s, 3H), 3.84 (s, 3H).

Workup

  1. temperatureheated to a refluxing temperature overnight
  2. concentrationThe resulting brown suspension was concentrated
  3. custompurified by MPLC (10-40% EtOAc in heptane

Sources & evidence

ORD record
ord-b6905986b4494e7db182a02622632abc
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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