Bromine → 4-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7821

Reaction equation

HRID 7821 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:12]([CH3:16])([CH2:13]2)[CH2:11][CH2:10][C:9](=[O:17])[CH:8]=3)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].[Br:23]Br>C(Cl)Cl.CCOC(C)=O>[Br:23][C:8]1[C:9](=[O:17])[CH2:10][CH2:11][C:12]2([CH3:16])[C:7]=1[C:6]1[C:14](=[CH:15][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:13]2

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 219909037-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 219908604-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 46.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (32 mg, 0.14 mmol) and NaHCO3 (60 mg, 0.7 mmol) in CH2Cl2 (0.5 ml) was treated with bromine (0.008 mL, 0.154 mmol), and the resulting mixture was stirred at room temperature for 22 hours. The mixture was diluted with EtOAc (8 ml), washed with dilute aqueous Na2S2O3 (4 mL) and brine (4 ml), dried over MgSO4, filtered, and evaporated under vacuum to a yellow oil (43 mg). This material was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing twice with CH2Cl2, to afford 4-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (20 mg) as a gum. The product was contaminated with a trace of 4,6-dibromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

Workup

  1. washwashed with dilute aqueous Na2S2O3 (4 mL) and brine (4 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to a yellow oil (43 mg)
  5. customThis material was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate

Sources & evidence

ORD record
ord-ca78e012a7fe470cbc127bc7a9674487
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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