N-bromobutanimide → 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372519Notes

Reaction equation

HRID 1372519 reaction equation
[C:1]([NH:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[CH:10]=3)=[CH:7][C:6]=1[F:23])(=[O:3])[CH3:2].[Br:24]N1C(=O)CCC1=O>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[C:10]=3[Br:24])=[CH:7][C:6]=1[F:23])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 179726807-(acetylamino)-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 179727237-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 122.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step 1 (1.1 g, approx. 3.5 mmol) was dissolved in anhydrous CH2Cl2 (11 mL) and the solution was purged with N2, cooled in an ice bath, and treated with N-bromosuccinimide (0.498 g, 2.8 mmol). After stirring at 0–5° C. for one hour, the reaction mixture was partitioned between water (150 mL) and EtOAc (150 mL). The organic portion was washed with aqueous 5% NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum to provide crude 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (1.35 g).

Workup

  1. customthe solution was purged with N2
  2. temperaturecooled in an ice bath
  3. customthe reaction mixture was partitioned between water (150 mL) and EtOAc (150 mL)
  4. washThe organic portion was washed with aqueous 5% NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-1e0ed76bfc7748078960b29ce8370a93
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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