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

HRID 2406503Notes

Reaction equation

HRID 2406503 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-96d4b3908c694c299770ada0b7e5f536
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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