2-Bromopyridine → HCID 20310424, compound

HRID 1763464Notes

Reaction equation

HRID 1763464 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[C:13]1([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1>CCOCC>[C:13]1([C:19]2[CH:20]=[CH:21][C:22]([C:23](=[O:24])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:26][CH:27]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 2779154-(cyclohex-1-en-1-yl)benzoic acidHCID 178418339Butyllithium

Product 1

HCID 20310424HCID 20310424, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

40 g of 2-bromopyridine in 50 ml of absolute ether are added dropwise slowly at -60° C with stirring and in a nitrogen atmosphere to 175 ml of a 1.5 N solution of butyl-lithium in ether, followed, 15 minutes after the completion of the addition, by a solution of 15 g of p-(1-cyclohexenyl)-benzoic acid in 250 ml of absolute ether. The cooling bath is then removed, the reaction mixture is allowed to warm up to room temperature and it is stirred for 2 hours at room temperature. Working up is carried out by pouring the reacton solution onto a mixture of ice and ammonium chloride and partitioning it between ether and water. The ether phase is separated off and washed successively with water, 0.1 N sodium hydroxide solution and water, dried over sodium sulphate and evaporated under reduced pessure. Distillation under reduced pressure of the evaporation residue yields, in the fraction boiling at 200° C (0.9 mm Hg), crude 2-{[p-(1-cyclohexenyl)-phenyl]-oxomethyl}-pyridine of the formula ##STR3## of melting point 58°-60° C.

Workup

  1. additionafter the completion of the addition
  2. customThe cooling bath is then removed
  3. additionby pouring the reacton solution
  4. additiononto a mixture of ice and ammonium chloride
  5. custompartitioning it between ether and water
  6. customThe ether phase is separated off
  7. washwashed successively with water, 0.1 N sodium hydroxide solution and water
  8. dry with materialdried over sodium sulphate
  9. customevaporated under reduced pessure
  10. distillationDistillation under reduced pressure of the evaporation residue

Sources & evidence

ORD record
ord-1909dd41fe33442abab50f01df4ea897
Source dataset
uspto-grants-1978_09
Patent number
US04112099

Reaction notes

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