Toluene → 2-Bromo-9,9-diethylfluorene

HRID 720015

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-].[Na+].I[CH2:18][CH3:19].[C:20]1(C)C=CC=C[CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:18][CH3:19])([CH2:20][CH3:21])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-bromofluorene (2.5 g, 10 mmol) in toluene (40 ml) was added tetrabutylammonium bromide (0.8 g, 2.48 mmol) as a phase transfer catalyst. A freshly prepared solution of aqueous sodium hydroxide (25 ml, 50% w/w) was added at once to the solution. The mixture turned orange and became viscous. To this solution, iodoethane (2.4 ml, 30 mmol) was added. The mixture was stirred at 60° C. for a period of 8 h. It was diluted with ethyl acetate (25 ml) and washed several portions of water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product liquid. The products were purified by column chromatography (silica gel, hexane as eluent, Rf=0.8 on thin layer chromatography) giving colorless oil of 2-bromo-9,9-diethylfluorene (2.5 g) in a yield of 82%.

Workup

washwashed several portions of water
dry with materialOrganic layer was dried over magnesium sulfate
concentrationconcentrated in vacuuo
customto afford the crude product liquid
customThe products were purified by column chromatography (silica gel, hexane as eluent, Rf=0.8 on thin layer chromatography)

Sources & evidence

ORD record: ord-ba321da493ae41c39fd83ed158c1ffdf
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132572B2

Linked notes

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