Methanol → Methyl 3-bromo-6-methylpyridine-2-carboxylate

HRID 2175951Notes

Reaction equation

HRID 2175951 reaction equation
[Br:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:16]O>>[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:16])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 219014933-Bromo-6-methylpyridine-2-carboxylic acid

Product 1

HCID 90404668Methyl 3-bromo-6-methylpyridine-2-carboxylateYield 40%

Procedure

To the title compound of step A (10.3 g, 20 mmol) in MeOH (50 mL) was added thionyl chloride (4.4 mL, 60 mmol). The reaction was heated at reflux overnight, cooled to rt and concentrated. Purification via silica gel chromatography (0-15% EtOAc in heptane) gave the title compound (1.9 g, 40%). MS (ESI) mass calcd. for C8H8BrNO2, 230.1; m/z found 232 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. customPurification via silica gel chromatography (0-15% EtOAc in heptane)

Sources & evidence

ORD record
ord-a0bd03346d534967a6f059138ca7e3ca
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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