Carbon Dioxide → 6-Methylbenzo[b]thiophene-3-carboxylic acid

HRID 1583347노트

반응식

HRID 1583347 반응식
C([Li])CCC.Br[C:7]1[C:8]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:9]=2[S:10][CH:11]=1.[C:17](=[O:19])=[O:18]>CCOCC>[CH3:16][C:13]1[CH:14]=[CH:15][C:8]2[C:7]([C:17]([OH:19])=[O:18])=[CH:11][S:10][C:9]=2[CH:12]=1

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 12398618HCID 12398618, 화합물HCID 178418339Butyllithium

생성물 1

HCID 136629696-Methylbenzo[b]thiophene-3-carboxylic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-70 °C

실험 절차

A solution of n-butyl lithium (15 ml. of 1.0M solution in hexane) was added dropwise to a stirred solution of 3-bromo-6-methylbenzo[b]thiophene (3.0 g.) in dry ether (40 ml.) at -70° C. under an atmosphere of dry nitrogen. The mixture was stirred at -70° C. for 30 minutes and then an excess of crushed solid carbon dioxide was added. When all the carbon dioxide had evaporated, water (25 ml.) was added and the mixture was stirred for a few minutes. The organic layer was separated and washed with 2N.NaOH solution. The aqueous layer and NaOH extract were combined and acidified with concentrated hydrochloric acid. The solid was filtered off, washed with water, dried and crystallized from toluene to give 6-methylbenzo[b]thiophene-3-carboxylic acid (1.60 g.), m.p. 205°-209°.

후처리

  1. customWhen all the carbon dioxide had evaporated
  2. additionwater (25 ml.) was added
  3. stirringthe mixture was stirred for a few minutes
  4. customThe organic layer was separated
  5. washwashed with 2N
  6. extractionThe aqueous layer and NaOH extract
  7. filtrationThe solid was filtered off
  8. washwashed with water
  9. customdried
  10. customcrystallized from toluene

출처 및 근거

ORD 기록
ord-5812d4a043464c9bb52807ab79049fe1
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551468

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