2-Bromo-2-methylpropionyl bromide → HCID 71089296, compound

HRID 1410313Notes

Reaction equation

HRID 1410313 reaction equation
[CH2:1]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[C:27]([CH3:32])([CH3:31])[C:28](Br)=[O:29].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[CH2:20]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]3[C:28](=[O:29])[CH:27]([CH3:32])[CH2:31][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 886852-Bromo-2-methylpropionyl bromideHCID 51284499,9-dihexylfluoreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 71089296HCID 71089296, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A 2000 mL round flask was charged with 9,9-dihexyl-9H-fluorene (79 g, 236.2 mmol) and 2-bromo-2-methylpropanoyl bromide (54.3 g, 236.2 mmol), and then dissolved with 600 mL of carbon disulfide inputted thereto. Then, the reactor was cooled with ice water. Under nitrogen atmosphere, aluminum trichloride (78.7 g, 590.4 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, followed by washing 3 times with 500 mL of distilled water. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials and drying, to thereby obtain 89.0 g of 9,9-dihexyl-2-methyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (yield: 93.6%) as highly viscous oil.

Workup

  1. customthe reaction was terminated by addition of 500 mL of distilled water
  2. washby washing 3 times with 500 mL of distilled water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customfollowed by removal of volatile materials
  5. customdrying

Sources & evidence

ORD record
ord-04b861cf498b45b0b88cb5382337fd4f
Source dataset
uspto-grants-2014_12
Patent number
US08921499B2

Reaction notes

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