Methanol → Methyl 2-(5-bromopyridin-3-yl)acetate

HRID 445767

Reaction equation

HRID 445767 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

Procedure

A mixture of (5-bromo-pyridin-3-yl)-acetic acid (ABCR, Karlsruhe, Germany, 4.54 mmol) and concentrated sulfuric acid (0.02 ml) in MeOH was refluxed for 13.5 h. The RM was concentrated, taken in EtOAc and sonicated. The organic layer was washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a brown oil. (HPLC: tR 2.21 min (Method A); M+H=230, 232 MS-ES)

Workup

  1. temperaturewas refluxed for 13.5 h
  2. concentrationThe RM was concentrated
  3. customsonicated
  4. washThe organic layer was washed with saturated aqueous NaHCO3, with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f336233cdd9e4e0db0c80e3722d06f41
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Linked notes

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