Carbon Dioxide → Benzo(b)thiophene-3-carboxylic acid

HRID 464749

반응식

HRID 464749 반응식
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.CI.[Mg].[C:14](=[O:16])=[O:15].Cl>CCOCC.C1(C)C=CC=CC=1>[S:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([C:14]([OH:16])=[O:15])=[CH:3]1

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 123250Benzo(b)thiophene, 3-bromo-HCID 5462224Magnesium

생성물 1

HCID 601280Benzo(b)thiophene-3-carboxylic acid수율 44%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 3-bromobenzothiophene (0.40 mole, (D15)) and methyl iodide (25 ml, 0.40 mole) in dry ether (400 ml) was added to a stirred mixture of magnesium turnings (24 g, 1.0 mole) and dry ether (100 ml) under nitrogen, at such a rate as to maintain a steady reflux. After the addition was complete, the reaction mixture was heated under reflux for 30 minutes and then allowed to cool to room temperature. The solution was diluted with dry toluene (500 ml) and stirred vigorously as dry carbon dioxide was bubbled through over 3 hours. The thick precipitate which formed was dissolved by the addition of dilute hydrochloric acid and the organic layer was then separated. The aqueous solution was extracted with ethyl acetate (2×300 ml) and all the organic solutions were then combined and extracted with 10% sodium carbonate solution (4×300 ml). The aqueous extracts were combined, washed with ether (2×200 ml) and then acidified with dilute hydrochloric acid. The precipitate was filtered off, washed with water and then dried under vacuum to give the title compound as a white solid (31.2 g, 44%) m.p. 171°-173°.

후처리

  1. temperatureat such a rate as to maintain a steady reflux
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. customwas bubbled through over 3 hours
  6. customThe thick precipitate which formed
  7. customthe organic layer was then separated
  8. extractionThe aqueous solution was extracted with ethyl acetate (2×300 ml) and all the organic solutions
  9. extractionextracted with 10% sodium carbonate solution (4×300 ml)
  10. washwashed with ether (2×200 ml)
  11. filtrationThe precipitate was filtered off
  12. washwashed with water
  13. customdried under vacuum

출처 및 근거

ORD 기록
ord-61428b7594504909ae8ab63384ed4ea3
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548948

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