Bromine → Anthracene, 9-bromo-2,6-bis(1,1-dimethylethyl)-

HRID 1028858Notes

Reaction equation

[Br:1]Br.[C:3]([C:7]1[CH:20]=[CH:19][C:18]2[C:9](=[CH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=3)[CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]2[C:16]([CH:17]=[C:18]3[C:9]=1[CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:20]=[CH:19]3)=[CH:15][C:14]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=2

Participants

Conditions

Temperature: 0 °C

Procedure

Bromine (3.02 g, 18.9 mmol) is added at 0° C. to a solution of 2,6-di-tert-butylanthracene (5.0 g, 17.2 mol) in carbontetrachloride (200 ml). The mixture is then stirred at 0° C. for 15 hours. After allowing to heat up to room temperature, half the amount of solvent is evaporated and the resulting mixture is poured into methanol. The precipitate is collected by filtration, recrystallized from n-hexane/methanol and the desired product is obtained as a white solid (1.13 g).

Workup

temperatureto heat up to room temperature
customhalf the amount of solvent is evaporated
additionthe resulting mixture is poured into methanol
filtrationThe precipitate is collected by filtration
customrecrystallized from n-hexane/methanol

Sources & evidence

ORD record: ord-709f0ddc475f4e589f500a2a936a0e82
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735610B2

Reaction notes

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