Acetic Anhydride → 2-Bromopyridin-3-yl acetate

HRID 1192400Notes

Reaction equation

HRID 1192400 reaction equation
[OH:1][C:2]1[C:3]([Br:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].C([O-])([O-])=O.[Na+].[Na+]>>[Br:8][C:3]1[C:2]([O:1][C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 154718962-Bromopyridin-3-yl acetateYield 99%

Procedure

A solution of 3-hydroxy-2-bromopyridine (21.4 g, 123 mmol) in acetic anhydride (25 g, 245 mmol) was refluxed for 1 hour. After cooling, the mixture was poured into ice water, neutralized with Na2CO3 and extracted with ether. The organic phase was dried and concentrated. The residue was subject to column chromatography, eluted by ether to afford Acetic acid 2-bromo-pyridin-3-yl ester (26.2 g, 99%). 1H NMR (CDCl3, 400 mHz) δ 8.28 (m, 1H), 7.46 (m, 1H), 7.30 (m, 1H), 2.38 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. washeluted by ether

Sources & evidence

ORD record
ord-e4508f3d28f04322be7ef468025785e7
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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