Bromine → 4-bromo-10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone

HRID 2113680Notes

Reaction equation

HRID 2113680 reaction equation
[CH2:1]([C:5]12[CH2:18][CH2:17][C:16](=[O:19])[CH:15]=[C:14]1[C:13]1[C:8](=[CH:9][C:10]([O:20][CH3:21])=[CH:11][CH:12]=1)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+].[Br:27]Br>C(Cl)(Cl)(Cl)Cl>[Br:27][C:15]1[C:16](=[O:19])[CH2:17][CH2:18][C:5]2([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]=1[C:13]1[C:8](=[CH:9][C:10]([O:20][CH3:21])=[CH:11][CH:12]=1)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 5860405910a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone

Product 1

HCID 586040514-bromo-10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone (31 mg, 0.109 mmol) and NaHCO3 (46 mg, 0.545 mmol) in CCl4 (0.25 mL) was stirred at room temperature while Br2 (0.0056 mL, 0.109 mmol) was added by syringe. A gummy precipitate formed which slowly dissolved. After stirring at room temperature for 15 minutes, the mixture was partitioned between EtOAc (4 mL) and aqueous Na2SO3 (4 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to an oil. The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 5% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc and the eluant was evaporated under vacuum to provide 4-bromo-10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone as an oil.

Workup

  1. additionwas added by syringe
  2. customA gummy precipitate formed which
  3. dissolutionslowly dissolved
  4. customthe mixture was partitioned between EtOAc (4 mL) and aqueous Na2SO3 (4 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under vacuum to an oil
  9. customThe crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  10. washThe UV visible product band was eluted with EtOAc
  11. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-d3ed259eb7e3489f9c44c322341ee100
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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