Water → 2-Bromo-3-decanyldithieno[3,2-b:2',3'-d]thiophene
Reaction equation
[CH2:1]([C:11]1[C:18]2[S:17][C:16]3[CH:19]=[CH:20][S:21][C:15]=3[C:14]=2[S:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:22]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:22][C:12]1[S:13][C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[S:17][C:18]=2[C:11]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-decanyldithieno[3,2-b:2′,3′-d]thiophene (91) (9.03 g, 0.027 mol) was dissolved in DMF (100 mL). To this solution, N-bromosuccinimide (NBS) (4.78 g, 0.027 mol) in DMF(50 mL) was added dropwise in the dark under argon. The resulting mixture was stirred at 0° C. for three hours. GC/MS showed a single peak at 415. This solution was poured into water (500 mL). Organic solution was extracted with hexane (3'100 mL). The combined organic solutions were washed with brine (2×50 mL) and water (50 mL). After drying over MgSO4, the hexane was evaporated. The crude product was purified by column chromatography and eluted with hexane to yield the target compound (10.1 g, 90.2%). 1H NMR: solvent, CD2Cl2. δ 7.39 (d, 1H), 7.29 (d, 1H), 2.74 (t, 2H), 1.74-1.33 (m, 16H), 0.89 (t, 3H). 13C NMR: 140.89, 140.63, 136.00, 131.55, 129.22, 126.58, 121.04, 108.89, 32.31, 29.94, 29.73 (overlap), 29.35, 28.49, 23.09, 14.27.
Workup
- extractionOrganic solution was extracted with hexane (3'100 mL)
- washThe combined organic solutions were washed with brine (2×50 mL) and water (50 mL)
- dry with materialAfter drying over MgSO4
- customthe hexane was evaporated
- customThe crude product was purified by column chromatography
- washeluted with hexane
Sources & evidence
- ORD record
- ord-4ad11e04b807438d9bc64507baf28337
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838623B2
Reaction notes
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