Bromine → 3-BROMO-8a-BUTYL-6-HYDROXY-8,8a-DIHYDROCYCLOPENTA[a]INDEN-2(1H)-ONE

HRID 2113646Notes

Reaction equation

HRID 2113646 reaction equation
[Br:1]Br.[CH2:3]([C:7]12[CH2:19][C:18](=[O:20])[CH:17]=[C:8]1[C:9]1[CH:10]=[CH:11][C:12]([OH:16])=[CH:13][C:14]=1[CH2:15]2)[CH2:4][CH2:5][CH3:6].C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:17]1[C:18](=[O:20])[CH2:19][C:7]2([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:15][C:14]3[CH:13]=[C:12]([OH:16])[CH:11]=[CH:10][C:9]=3[C:8]=12

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 58604056HCID 58604056, compound

Product 1

HCID 98185443-BROMO-8a-BUTYL-6-HYDROXY-8,8a-DIHYDROCYCLOPENTA[a]INDEN-2(1H)-ONE

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Bromine (0.005 mL, 0.095 mmol) was added to an ice-cold mixture of 8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (23 mg, 0.095 mmol) and NaHCO3 (40 mg, 0.48 mmol) in CCl4 (0.3 mL). The resulting mixture was stirred at 0-5° C. for 45 minutes, then diluted with CH2Cl2 (30 mL) and washed with water (30 mL). The aqueous phase was back-extracted with CH2Cl2 (2×10 mL). The combined organics were washed with saturated aqueous Na2S2O3, dried over MgSO4, filtered, and evaporated under vacuum to provide an off-white solid. Recrystallization from hexane/CH2Cl2 afforded 3-bromo-8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as small, white needles.

Workup

  1. washwashed with water (30 mL)
  2. extractionThe aqueous phase was back-extracted with CH2Cl2 (2×10 mL)
  3. washThe combined organics were washed with saturated aqueous Na2S2O3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto provide an off-white solid
  8. customRecrystallization from hexane/CH2Cl2

Sources & evidence

ORD record
ord-78d4f57c2c634cd7916d7948997b3a2a
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…