Carbon Dioxide → HCID 14229718, compound

HRID 1761917Notes

Reaction equation

HRID 1761917 reaction equation
CI.[Mg].Br[C:5]1[C:13]2[O:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:20](=[O:22])=[O:21].Cl>O1CCCC1>[C:14]1([C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:20]([OH:22])=[O:21])[C:13]=3[O:12][CH:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 30163557-Bromo-3-phenylbenzofuranHCID 5462224Magnesium

Product 1

HCID 14229718HCID 14229718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3)-(i) 2.4 ml of methyl iodide are added dropwise to a solution of 3.9 g of magnesium in 16 ml of tetrahydrofuran and the mixture is stirred at room temperature for 20 minutes. A solution of 11.0 g of 7-bromo-3-phenylbenzofuran in tetrahydrofuran is added dropwise to the mixture and the mixture is refluxed for 4 hours. After cooling, the reaction mixture is poured to dry ice, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is recrystallized from ethyl acetate to give 6.31 g of 3-phenylbenzofuran-7-carboxylic acid as pale yellow prisms.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-54a4d49071b34d5288a8b718030a7365
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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