2-Bromo-2-methylpropionyl bromide → HCID 71089295, compound

HRID 1410322Notes

Reaction equation

HRID 1410322 reaction equation
[CH2:1]([C:15]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[C:43]([CH3:48])([CH3:47])[C:44](Br)=[O:45].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[CH3:47][CH:43]1[C:44](=[O:45])[C:25]2=[CH:26][C:27]3[C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:16]4[C:21]([C:22]=3[CH:23]=[C:24]2[CH2:48]1)=[CH:20][CH:19]=[CH:18][CH:17]=4

Participants

5

Reactant 3

HCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) ChlorideHCID 22568527HCID 22568527, compound

Product 1

HCID 71089295HCID 71089295, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A 5000 mL round flask was charged with 9,9-ditetradecyl-9H-fluorene (30 g, 53.7 mmol) and 2-bromo-2-methylpropanoyl bromide (12.7 g, 55.3 mmol), and then dissolved with 300 mL of carbon disulfide inputted thereto. Then, the reactor was cooled with ice water. Under nitrogen atmosphere, aluminum trichloride (15.7 g, 118.1 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 100 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, to thereby obtain 30.0 g of 2-methyl-9,9-ditetradecyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (yield: 89.1%) as highly viscous oil.

Workup

  1. customthe reaction was terminated by addition of 100 mL of distilled water
  2. washby washing with 500 mL of distilled water three times
  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-04ded70bd1aa4ce8a7facb0ca85e7f77
Source dataset
uspto-grants-2014_12
Patent number
US08921499B2

Reaction notes

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