Benzoyl Peroxide → 6-(Bromomethyl)-3-pyridinecarboxylic acid

HRID 632990Notes

Reaction equation

HRID 632990 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CC(O)=O.C1C=CC=CC=1.C(OCC)(=O)C>[Br:18][CH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1378606-Methylnicotinic acid

Product 1

HCID 218409786-(Bromomethyl)-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22229412AcOH benzeneSolvent

Conditions

Temperature
120 °C

Procedure

6-methylnicotinic acid (100 mg 0.14 mmol) was dissolved in 10% AcOH/benzene (1 mL) and treated with NBS (117 mg, 0.18 mmol) and benzoylperoxide (18 mg, 0.07 mmol). The reaction mixture was heated in a sealed microwave reactor at 120° C. for 1 min. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, dried (MgSO4), concentrated and purified by silica gel chromatography to yield 6-(bromomethyl)pyridine-3-carboxylic acid.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c2153e82fd6940b9a62d8abf423936ef
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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