Carbon Dioxide → 5-Bromo-4-methylnicotinic acid

HRID 1454934Notes

Reaction equation

HRID 1454934 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].C([Li])CCC.[C:15](=[O:17])=[O:16].O>C1COCC1.CCCCCC>[Br:9][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:7]=1[CH3:8])[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 8193383,5-Dibromo-4-methylpyridine2×HCID 178418339Butyllithium

Product 1

HCID 70606755-Bromo-4-methylnicotinic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under argon, a solution of 3,5-dibromo-4-methylpyridine (intermediate 10.1, 2.51 g, 10 mmol) in anhydrous THF (100 ml) is reacted at a temperature of −100° C. with a solution of n-butyllithium in hexane (1.6N, 6.5 ml). The reaction mixture is stirred for 15 min and then dry ice is added. The temperature is kept for 15 min at −85° C., for 1 h 30 min at −78° C. and for 2 h at room temperature. Water is added. The solvents are evaporated under vacuum and the residue is purified, eluting on diol grafted silica with MeOH.

Workup

  1. waitThe temperature is kept for 15 min at −85° C., for 1 h 30 min at −78° C. and for 2 h at room temperature
  2. customThe solvents are evaporated under vacuum
  3. customthe residue is purified
  4. washeluting on diol

Sources & evidence

ORD record
ord-353630f7d03144d0947379936724fc7c
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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