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

HRID 1055281Notes

Reaction equation

HRID 1055281 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

9,9-dihexyl-9H-fluorene (79 g, 236.2 mmol) and 2-bromo-2-methylpropanoyl bromide (54.3 g, 236.2 mmol) were injected into a 2000 mL round flask and then dissolved by adding 600 mL of carbon disulfide inputted thereto. Then, the reactor was cooled with ice water. Aluminum trichloride (78.7 g, 590.4 mmol) was slowly added thereto in ten lots over 2 hours under nitrogen atmosphere. Then, after the mixture was stirred at room temperature for 8 hours, the reaction was terminated by adding of 500 mL of distilled water, followed by washing with 500 mL of distilled water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials and drying, thereby obtaining 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. dissolutiondissolved
  2. customthe reaction was terminated
  3. additionby adding of 500 mL of distilled water
  4. washby washing 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

Sources & evidence

ORD record
ord-7e63d456170148a4ab568bdc32750bd4
Source dataset
uspto-grants-2016_07
Patent number
US09394388B2

Reaction notes

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