Butyl iodide → (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine

HRID 221162Notes

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]>>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:15]([CH2:4][CH2:3][CH2:2][CH3:14])[CH2:10][CH2:9][CH2:8][CH3:7])=[CH:10][C:11]=3[C:12]2([CH2:13][CH2:5][CH2:6][CH3:11])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 10962Butyl iodide

HCID 231262-Amino-7-bromofluorene

Product 1

HCID 58239559(7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine

Procedure

As shown in Scheme 2, 7-bromo-9H-fluoren-2-ylamine is reacted with 1-iodobutane to form (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21). Then, (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21) is reacted with 5-formyl-2-thiopheneboronic acid by Suzuki coupling reaction to obtain 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a). Finally, in acetonitrile, 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a) is reacted with cyanoacetic acid by using piperidine as a catalyst, to obtain 2-Cyano-3-[5-(9,9-dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]-acrylic acid (23a).

Sources & evidence

ORD record: ord-5fce3db293b743f294c6f6485994e3e3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08203068B2

Reaction notes

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