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

HRID 2406503ノート

反応式

HRID 2406503 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-96d4b3908c694c299770ada0b7e5f536
出典データセット
uspto-grants-2014_08
特許番号
US08809376B2

反応ノート

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