Carbon Dioxide → 6-Bromopyridine-2-carboxylic acid

HRID 741816Notes

Reaction equation

HRID 741816 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li]CCCC.[C:14](=[O:16])=[O:15]>>[Br:8][C:4]1[N:3]=[C:2]([C:14]([OH:16])=[O:15])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 5939196-Bromopyridine-2-carboxylic acidYield 63.4%

Procedure

To a suspension of 2,6-dibromopyridine (59 g, 0.25 mol) in ET2O (600 mL) at -70° C. there was added slowly n-BuLi 2.12M in hexanes (118 mL, 0.25 mol); the resulting mixture was stirred in the cold until a solution was obtained (45 min.); this mixture was poured onto a slurry of crushed dry ice (200 g) in ET2O (500 mL). The resulting suspension was allowed to warm up, then it was extracted with H2O (500 mL, then 250 mL). The combined aqueous extracts were extracted with Et2O, then acidified with 12N HCl, affording a precipitate which was filtered. This beige solid was washed with H2O and dried to afford the title acid (32 g), m.p. 186°-189° C.

Workup

  1. customwas obtained (45 min.)
  2. temperatureto warm up
  3. extractionit was extracted with H2O (500 mL
  4. extractionThe combined aqueous extracts were extracted with Et2O
  5. customaffording a precipitate which
  6. filtrationwas filtered
  7. washThis beige solid was washed with H2O
  8. customdried

Sources & evidence

ORD record
ord-aac989e60bd74cfd9277697f467deb15
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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