Sodium methanethiolate → 4-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

HRID 2406503노트

반응식

HRID 2406503 반응식
C[S-].[Na+].[Br:4][C:5]1[C:13]([O:14]C)=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:16]>CN(C)C=O>[Br:4][C:5]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:16]

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 378189874-bromo-5-methoxy-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 688667904-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

Sodium methanethiolate (2.00 g) is added to a microwave vial charged with a stir bar, 4-bromo-5-methoxy-indan-1-one (1.58 g), and N,N-dimethylformamide (10 mL). The vial is sealed and the mixture is heated to 130° C. and stirred at this temperature for 2 h. After cooling to room temperature, the mixture is partitioned between ethyl acetate and 1 N aqueous HCl solution. The aqueous phase is separated and extracted with ethyl acetate. The combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated and the residue is triturated with diethylether. The precipitate is filtered off and dried in vacuo to give the title compound. LC (method 1): tR=0.84 min; Mass spectrum (ESI+): m/z=227/229 (Br) [M+H]+.

후처리

  1. additionvial charged with a stir bar
  2. customThe vial is sealed
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between ethyl acetate and 1 N aqueous HCl solution
  5. customThe aqueous phase is separated
  6. extractionextracted with ethyl acetate
  7. washThe combined organic phases are washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvents are evaporated
  10. customthe residue is triturated with diethylether
  11. filtrationThe precipitate is filtered off
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-96d4b3908c694c299770ada0b7e5f536
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809376B2

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