N-bromobutanimide → 4-Bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone

HRID 7889Notes

Reaction equation

HRID 7889 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18]([OH:22])[CH:19]=2)[C:14]1=[O:24])[CH2:10][CH2:11][CH3:12]>CN(C)C=O>[Br:1][C:19]1[C:18]([OH:22])=[C:17]([F:23])[CH:16]=[C:15]2[C:20]=1[CH2:21][CH:13]([CH2:9][CH2:10][CH2:11][CH3:12])[C:14]2=[O:24]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 219908852-Butyl-6-fluoro-5-hydroxy-1-indanone

Product 1

HCID 219908524-Bromo-2-butyl-6-fluoro-5-hydroxy-1-indanoneYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (1.41 g, 7.93 mmol) was added to a solution of 2-butyl-6-fluoro-5-hydroxy-1-indanone (1.76 g, 7.93 mmol) in anhydrous N,N-dimethylformamide (15 mL). The resulting solution was stirred at room temperature for two hours. The solvent was evaporated under vacuum and the residue was partitioned between EtOAc (100 mL) and water (100 ml). The organic phase was washed with water (4×100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide crude 4-bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone (2.17 g) as an oil.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was partitioned between EtOAc (100 mL) and water (100 ml)
  3. washThe organic phase was washed with water (4×100 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-003b390b794440cdb243ce9841e7b453
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

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