Water → HCID 58194202, compound

HRID 68523Notes

Reaction equation

HRID 68523 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:18]3[C:9](=[CH:10][C:11]4[C:16]([CH:17]=3)=[CH:15][C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][CH:12]=4)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:27]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:27][C:17]1[C:18]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]=[CH:12]3)=[CH:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:20][CH:19]=2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 149154562,6-Diphenylanthracene

Product 1

HCID 58194202HCID 58194202, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

First, 33.0 g of 2,6-diphenylanthracene were dissolved in 200 mL of N,N-dimethylformamide under heat, and then a solution of 18.0 g of N-bromosuccinimide in 20 mL of N,N-dimethylformamide was added to the solution. The mixture was stirred at 60° C. for 6 hours under heat. After having been cooled to room temperature, the reaction solution was poured into 1 L of water. The resultant solid was sequentially washed with methanol, water, and methanol. After that, the solid was repeatedly recrystallized with toluene and hexane and washed. Thus, 33.5 g of 9-bromo-2,6-diphenylanthracene were obtained (in 82% yield).

Workup

  1. temperatureunder heat
  2. temperatureunder heat
  3. temperatureAfter having been cooled to room temperature
  4. washThe resultant solid was sequentially washed with methanol, water, and methanol
  5. customAfter that, the solid was repeatedly recrystallized with toluene and hexane
  6. washwashed

Sources & evidence

ORD record
ord-c256786fceaf4707a367cfde7c1799e0
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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