Propylene Carbonate → 2-Bromo-9,9-diethylfluorene

HRID 1871164Notes

Reaction equation

HRID 1871164 reaction equation
C([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[C:4]=1[CH2:16][CH3:17])C.[Br:18]N1C(=O)CCC1=O.C1(=O)O[CH:29]([CH3:30])CO1>O>[Br:18][C:3]1[CH:4]=[CH:16][C:17]2[C:11]3[C:12](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:13]([CH2:29][CH3:30])([CH2:5][CH3:6])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 7924Propylene CarbonateHCID 67184N-bromobutanimideHCID 23440471HCID 23440471, compound

Product 1

HCID 121238752-Bromo-9,9-diethylfluoreneYield 89.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethylfluorene (22.2 g., 0.1 mol.) in propylene carbonate (100 ml), N-bromosuccinimide (17.8 g., 0.1 mol.) was added at 57° C. in portions and the mixture was stirred for 30 minutes at 60° C. The mixture was diluted with 1200 ml of water and extracted with 500 ml of toluene. The toluene extract was washed 3 times with 300 ml portions of water, dried and concentrated. The crude product from 3 batches of the same size totaled 117 g. oil. This was distilled at 2 mm. The first fraction, b.p. 90-93° C., 22.33 g., was found to be propylene carbonate. The second fraction, b. p. 155-165° C., 81.0 g. (89.7% yield), was the desired compound. Mass Spec: m/z 300, 302 (M+).

Workup

  1. extractionextracted with 500 ml of toluene
  2. extractionThe toluene extract
  3. washwas washed 3 times with 300 ml portions of water
  4. customdried
  5. concentrationconcentrated
  6. distillationThis was distilled at 2 mm

Sources & evidence

ORD record
ord-e100283aff2a4889b6f7fa78ddaf2952
Source dataset
uspto-grants-2000_08
Patent number
US06100405

Reaction notes

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