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

HRID 1669920Notes

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-803fa8132095421fa79918f00ba10389
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989644B2

Reaction notes

Loading…