Bromine → HCID 18424469, compound

HRID 1282462Notes

Reaction equation

HRID 1282462 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]Br>ClCCCl>[Br:18][C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 13149942HCID 13149942, compound

Product 1

HCID 18424469HCID 18424469, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a reactor were introduced 8.81 g (39.6 mmol) of the 1,1-diphenyl-3-methylbutene and 35 mL of 1,2-dichloroethane under a nitrogen atmosphere. The contents were cooled to 0° C., and 6.33 g (39.6 mmol) of bromine was gradually added dropwise thereto. This mixture was stirred at room temperature for 1 hour. The resultant reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol and ethyl acetate to obtain 8.64 g (72%) of the target compound as white crystals.

Workup

  1. customThe resultant reaction mixture
  2. washwas washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThereafter, the solvent was removed under reduced pressure
  5. customThe concentrate was recrystallized from ethanol and ethyl acetate

Sources & evidence

ORD record
ord-28088487e6564a62adbbad9432c5ed3d
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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