9,9-Dimethylfluorene → HCID 71089313, compound

HRID 2273379Notes

Reaction equation

HRID 2273379 reaction equation
[CH3:1][C:2]1([CH3:15])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.Br[C:17]([CH3:22])([CH3:21])[C:18](Br)=[O:19].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[CH3:21][CH:17]1[C:18](=[O:19])[C:5]2=[CH:4][C:3]3[C:2]([CH3:15])([CH3:1])[C:14]4[C:9]([C:8]=3[CH:7]=[C:6]2[CH2:22]1)=[CH:10][CH:11]=[CH:12][CH:13]=4

Participants

5

Reactant 3

HCID 783259,9-DimethylfluoreneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 71089313HCID 71089313, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A 2000 mL round flask was charged with 9,9-dimethyl-9H-fluorene (50 g, 257.4 mmol) and 2-bromo-2-methylpropanoyl bromide (61.0 g, 265.1 mmol), and then dissolved with 700 mL of carbon disulfide inputted thereto. Then, the reactor was cooled with ice water. Under nitrogen atmosphere, aluminum trichloride (85.8 g, 643.4 mmol) was slowly added thereto in ten lots over 2 hours. The mixture was stirred at room temperature for 8 hours, and then the reaction was terminated by addition of 500 mL of distilled water. The resultant mixture was diluted by adding 500 mL of methyl chloride and washed with 500 mL of distilled water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials and drying, and then recrystallized by using methyl chloride and methanol, to thereby obtain 64.0 g of 2,9,9-trimethyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (yield: 94.8%) as white solid.

Workup

  1. customthe reaction was terminated by addition of 500 mL of distilled water
  2. additionThe resultant mixture was diluted
  3. additionby adding 500 mL of methyl chloride
  4. washwashed with 500 mL of distilled water three times
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customfollowed by removal of volatile materials
  7. customdrying
  8. customrecrystallized

Sources & evidence

ORD record
ord-3b6768017db14a7997893bc84f44d03a
Source dataset
uspto-grants-2015_09
Patent number
US09120884B2

Reaction notes

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