Water → HCID 58194480, compound

HRID 68524Notes

Reaction equation

[C:1]1([C:7]2[CH:20]=[CH:19][C:18]3[C:9](=[C:10]([C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=4)[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:37]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:37][C:17]1[C:18]2[C:9]([C:10]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)=[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:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:20][CH:19]=2

Participants

Conditions

Temperature: 60 °C

Procedure

First, 9.09 g of 2,6-diphenyl-9-(2-naphthyl)anthracene were dissolved in 100 mL of N,N-dimethylformamide under heat, and then a solution of 3.91 g of N-bromosuccinimide in 10 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 500 mL 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, 8.55 g of 9-bromo-2,6-diphenyl-10-(2-naphthyl)anthracene were obtained (in 80% yield).

Workup

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

Sources & evidence

ORD record: ord-c2878cde5988490cb4a2cc3d5b1f1037
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822041B2

Reaction notes

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