Tetrahydrofuran → 7-bromo-9,9-dibutyl-9H-fluoren-2-amine
Reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([NH2:15])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.I[CH2:17][CH2:18][CH2:19][CH3:20].CC(C)([O-])C.[K+].O1[CH2:31][CH2:30][CH2:29][CH2:28]1>O>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([NH2:15])=[CH:10][C:11]=3[C:12]2([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Under N2 atmosphere, 0.52 parts of 7-bromo-9H-fluoren-2-ylamine, 2.21 parts of 1-iodobutane, and 1.35 parts of potassium tert-butoxide were added into 20 parts of dry tetrahydrofuran, followed by stirring and mixing. Then, the reaction mixture was heated to 50° C. and reacted for 18 hours. After the reaction mixture was cooled, water was used for quenching the reaction, diethyl ether was used for extracting the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with column chromatography method by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (31) of the present example. This compound was in a form of a brown-yellow solid, and the yield of this compound was 79%.
Workup
- additionmixing
- customreacted for 18 hours
- temperatureAfter the reaction mixture was cooled
- customfor quenching
- customthe reaction, diethyl ether
- extractionfor extracting the product, and magnesium sulfate
- customAfter removing the solvent
- customthe residual was purified with column chromatography method
Sources & evidence
- ORD record
- ord-d1ac77785b76477d861df4663cc9adac
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08419808B2
Reaction notes
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