HCID 59844122, compound → HCID 59844102, compound
Reaction equation
[Br:1][C:2]1[C:6]2[S:7][C:8](C(O)=O)=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[S:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1>[Br:1][C:2]1[C:6]2[S:7][CH:8]=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[S:4][CH:3]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
In a 1 L three-neck round-bottom flask, the compound E (about 43.5 g, about 101 mmol) was placed, and dissolved in quinoline (about 250 ml), after which the solution was heated to about 200° C. and stirred for about 30 minutes. The stirred solution was cooled, and was then extracted with ethyl acetate (about 2 L), after which the extracted organic layer was washed two times with about 5 N hydrochloric acid solution (about 500 ml), washed with about 2N hydrochloric acid (about 500 ml), and washed with brine (about 500 ml). The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and then subjected to column chromatography using hexane, thus obtaining about 31.6 g (y=about 80%) of 6-bromo-3-dodecyl-thieno[3,2-b]thiophene F. 1H NMR of the obtained compound F was as follows.
Workup
- temperatureThe stirred solution was cooled
- extractionwas then extracted with ethyl acetate (about 2 L)
- washafter which the extracted organic layer was washed two times with about 5 N hydrochloric acid solution (about 500 ml)
- washwashed with about 2N hydrochloric acid (about 500 ml)
- washwashed with brine (about 500 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-acdd13f140fd4307abba07fc5a50440f
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008426B2
Reaction notes
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