Hydrochloric Acid → 5-Cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acid

HRID 1738682Notes

Reaction equation

HRID 1738682 reaction equation
[OH-:1].[Na+].BrBr.[C:5]([C:8]1[C:12]2[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:7])C.Cl>O.O1CCOCC1>[C:17]([C:14]1[CH:15]=[CH:16][C:11]2[O:10][C:9]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)=[C:8]([C:5]([OH:1])=[O:7])[C:12]=2[CH:13]=1)#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 218444313-Acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile

Product 1

HCID 218443945-Cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acidYield 34.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

5.2 g of sodium hydroxide was dissolved in 30 ml of water, and the solution was cooled to a temperature of 0° C. or below. With stirring, to this were added dropwise 2.7 ml of bromine and then 40 ml of a dioxane solution containing 4.14 g of 3-acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile obtained in the above step d). The resulting mixture was stirred at 0° C. for 45 minutes with ice cooling for 1 hour. The resulting reaction solution was mixed with water, adjusted to pH 2 with concentrated hydrochloric acid, and then extracted with chloroform. The resulting organic layer was washed with water and dried to distill off the solvent. Thereafter, the resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an eluant, thereby obtaining 1.44 g of 5-cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acid.

Workup

  1. temperaturethe solution was cooled to a temperature of 0° C. or below
  2. customobtained in the above step d)
  3. stirringThe resulting mixture was stirred at 0° C. for 45 minutes with ice cooling for 1 hour
  4. customThe resulting reaction solution
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with water
  7. customdried
  8. distillationto distill off the solvent
  9. customThereafter, the resulting residue was purified

Sources & evidence

ORD record
ord-f8e1688da9cd4f8c85f1f4adb2837598
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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