1,6-Dibromohexane → 2,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene

HRID 514168Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:10][CH2:11][CH2:12][CH2:4][CH2:3][CH2:2][Br:1])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1 (5.0 g, 15.43 mmol), 1,6-dibromohexane (30 mL), tetrabutylammonium bromide (TBAB) (0.5 g), and potassium hydroxide aqueous solution (30 mL, 50% w/w) was stirred at 70° C. for 24 h under nitrogen. After diluting the reaction mixture with dichloromethane, the organic layer was washed with water and brine. The separated organic layer was dried over magnesium sulfate, and dichloromethane was evaporated. The residual 1,6-dibromohexane was distilled in a vacuum, and compound 2 (5.67 g, 56.5%) was obtained as a white crystal by chromatography with hexane/CH2Cl2 (95:5) as the eluent; m.p. 68° C. 1H NMR (500 MHz, CDCl3). δ (ppm): 7.51 (d, 2H, J=8.0 Hz), 7.45 (d, 2H, J=8.0 Hz), 7.42 (s, 2H), 3.27 (t, 4H, J=7 Hz), 1.91 (t, 4H, J=8.5 Hz), 1.65 (p, 4H, J=8 Hz), 1.18 (p, 4H, J=8 Hz), 1.06 (p, 4H, J=7.5 Hz), 0.57 (m, 4H).

Workup

washthe organic layer was washed with water and brine
dry with materialThe separated organic layer was dried over magnesium sulfate, and dichloromethane
customwas evaporated
distillationThe residual 1,6-dibromohexane was distilled in a vacuum

Sources & evidence

ORD record: ord-0a2e70d02b8142bc9d4e1b53a944a2c9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09105851B2

Reaction notes

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