Acetic Acid → Methyl 2-bromopyridine-3-carboxylate

HRID 1809475Notes

Reaction equation

HRID 1809475 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11]C(O)=O>CCOCC.C1COCC1>[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:11])=[O:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2332622-Bromopyridine-3-carboxylic acid

Product 1

HCID 12349191Methyl 2-bromopyridine-3-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of CH2N2 (4 eq.) in Et2O (1 M) was added dropwise to a solution of 2-bromonicotinic acid in THF (0.5 M) at RT. The reaction mixture was stirred at room temperature overnight, then quenched by dropwise addition of AcOH (4 eq.). The organic phase was washed with water and brine and dried (MgSO4). Evaporation of the solvent yielded (75%) the title compound which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3, 300K) δ 8.47 (1H, dd, J=4.8 Hz, 2.1 Hz), 8.07 (1H, dd, J=7.8 Hz, 2.1 Hz), 7.35 (1H, dd, J=7.5 Hz, 4.5 Hz), 3.93 (3H, s).

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dd71a2d311634355aa5a17a81b55f724
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

Loading…