Bromine → 9a-(2-Bromoacetyl)-1,2,3,4,4a,9a-hexahydrofluoren-9-one

HRID 279147Notes

Reaction equation

HRID 279147 reaction equation
[Br:1]Br.[C:3]([C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]2=[O:19])(=[O:5])[CH3:4]>CO>[Br:1][CH2:4][C:3]([C:6]12[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]2=[O:19])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 226245739a-Acetyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one

Product 1

HCID 226245969a-(2-Bromoacetyl)-1,2,3,4,4a,9a-hexahydrofluoren-9-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine (1.2 ml) was added to a mixture of 9a-acetyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one (5 g) in methanol (20 ml) at 20-30° C. The reaction mixture was stirred for 2 hours and quenched with NaHCO3 solution (0.8 g NaHCO3 and 24 ml water). The mixture was extracted with CH2Cl2 (3×30 ml) and the organic phase was washed with water (30 ml) and dried over Na2SO4. Evaporation gave 6.6 g of the crude product which was used without further purification for the next step.

Workup

  1. customquenched with NaHCO3 solution (0.8 g NaHCO3 and 24 ml water)
  2. extractionThe mixture was extracted with CH2Cl2 (3×30 ml)
  3. washthe organic phase was washed with water (30 ml)
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-f6e88e08f8574d4087b59f47a73be797
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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