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

HRID 471435Notes

Reaction equation

HRID 471435 reaction equation
[Br:1][C:2]1[C:10]([O:11]C)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].C[S-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13]

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
120 °C

Procedure

4-Bromo-5-methoxy-indane-1-one (10 g, 41.48 mmol) and sodium methane-thiolate (12.68 g, 180.94 mmol) are dissolved in 25 mL of N,N-dimethylformamide and the reaction mixture is stirred at 120° C. for 3 h. The reaction mixture is concentrated under vacuum, 40 mL of a 2 M solution of hydrochloric acid is added and the reaction mixture is extracted with 300 mL of ethyl acetate. The organic phase is collected, dried over sodium sulfate and concentrated under vacuum. The crude product obtained (9 g) is used in the next step without any further treatment.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum, 40 mL of a 2 M solution of hydrochloric acid
  2. additionis added
  3. extractionthe reaction mixture is extracted with 300 mL of ethyl acetate
  4. customThe organic phase is collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ed0a5ff54fe34080a8f4a48370d79a39
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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