Carbon Dioxide → 2,3',5'-Trifluoro[1,1'-biphenyl]-4-carboxylic acid

HRID 1912238노트

반응식

HRID 1912238 반응식
C1COCC1.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[C:9]([F:21])[CH:8]=1.[C:22](=[O:24])=[O:23]>Cl>[F:21][C:9]1[CH:8]=[C:7]([C:22]([OH:24])=[O:23])[CH:12]=[CH:11][C:10]=1[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 58362061HCID 58362061, 화합물

생성물 1

HCID 532116502,3',5'-Trifluoro[1,1'-biphenyl]-4-carboxylic acid

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

In a reactor under an N2-atmosphere, 100 ml of a 1.3M THF solution of isopropyl magnesium chloride/lithium chloride complex (130 mmol) was added and then stirred at room temperature, 28.7 g (100 mmol) of 4-bromo-2,3′,5′-trifluoro-1,1′-biphenyl was slowly added, and then the mixture was stirred at room temperature for 2 hours. Next, while the mixture was cooled to 5-15° C. by an ice bath, dried CO2 gas was blown in without heat generation. The reaction solution was poured in 200 ml of 2N HCl(aq) and extracted by diethyl ether. After the organic layer was collected, washed by saturated saline and dried by anhydrous magnesium sulfate, it was filtered to remove the insoluble substance and concentrated under a reduced pressure. The residue was purified by a fractionation operation utilizing column chromatography, with ethyl acetate as an eluent solvent and silica gel as a filler. The product was further purified by recrystallization using heptane/ethanol in a volume ratio of 30/70, so that 10.3 g of 2,3′,5′-trifluoro-1,1′-biphenyl-4-carboxylic acid was obtained as a white solid.

후처리

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. temperatureNext, while the mixture was cooled to 5-15° C. by an ice bath
  3. temperaturewithout heat generation
  4. extractionextracted by diethyl ether
  5. customAfter the organic layer was collected
  6. washwashed by saturated saline
  7. dry with materialdried by anhydrous magnesium sulfate, it
  8. filtrationwas filtered
  9. customto remove the insoluble substance
  10. concentrationconcentrated under a reduced pressure
  11. customThe residue was purified by a fractionation operation utilizing column chromatography, with ethyl acetate as an eluent solvent and silica gel as a filler
  12. customThe product was further purified by recrystallization

출처 및 근거

ORD 기록
ord-8c7aa67660994966b019452db42c05f7
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609208B2

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