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

HRID 1844942Notes

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-deb3e4e97f9948fbb3cd94e5966d2d22
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946984B2

Reaction notes

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