2-Bromo-3-Dodecylthiophene → HCID 59428851, compound
Reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cu](C#N)[C:20]#[N:21]>>[C:20]([C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])#[N:21]Participants
3
Procedure
A reaction between 2-bromo-3-dodecylthiophene (Compound-1, 81.0 mmol) and excess copper cyanide (CuCN) produced 2-cyano-3-dodecylthiophene (Compound-2, 34% yield), which was heated and reacted with excess (approximately 2.5 equivalents) dithiophosphoric acid O,O′-diethylether in tetrahydrofuran (THF) solution for about 12 hours. The obtained 2-thioamino-3-dodecylthiophene (Compound-3, 45% yield) and 1.2 equivalents of bromooctanone were reacted to obtain 2-thiazole(3′-dodecyl)-3-dodecylthiophene (Compound-4, 32% yield), which was in turn reacted with N-bromosuccinimide (NBS) to obtain the thiophene-thioazol derivative (Compound-5, 82% yield). An NMR analysis result of the resultant product was as follows:
Sources & evidence
- ORD record
- ord-9003604b5c7549a4bcfb551a9c37a668
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07777221B2
Reaction notes
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