tert-Butanol → 4-[2-(4-Bromo-phenyl)-vinyl]-nicotinic acid

HRID 226266Notes

Reaction equation

HRID 226266 reaction equation
[H-].[Na+].C(O)(C)(C)C.[H][H].[CH3:10][C:11]1[C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=1.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>CN(C=O)C>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[CH:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 24758Sodium hydrideHCID 707414-BromobenzaldehydeHCID 409602Ethyl 4-methylnicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 688930134-[2-(4-Bromo-phenyl)-vinyl]-nicotinic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

0.9 g (22.5 mmol) of a 60% suspension of sodium hydride in paraffin are added to a solution of 2.25 g (30.40 mmol) of tertbutanol in 27.5 ml of DMF. The whole is heated in a water bath for 30′ till the evolution of hydrogen ends. The system is cooled at 0° C. and 2.5 g (15.13 mmol) of ethyl 4-methylnicotinate in 2.5 ml of DMF are dropped with stirring. After 1.5 hr stirring at the same temperature, 3.4 g (18.37 mmol) of 4-bromobenzaldehyde in 2.5 ml DMF are dropped. The system is stirred at room temperature overnight. The solution is poured over 100 g of ice and is filtered. The filtrate is acidified with acetic acid and the solid is filtered, washed with water and dried, yielding 1.85 g (40%) of a product that is used directly in the next step.

Workup

  1. additionare dropped
  2. stirringThe system is stirred at room temperature overnight
  3. filtrationis filtered
  4. filtrationthe solid is filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-279ec97862df4feb873898accdfde879
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Reaction notes

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