Water → 2-Bromo-3-decanyldithieno[3,2-b:2',3'-d]thiophene

HRID 83967Notes

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

Conditions

Temperature: 0 °C

Procedure

3-decanyldithieno[3,2-b:2′,3′-d]thiophene (91) (9.03 g, 0.027 mol) is dissolved in DMF (100 mL). To this solution, N-bromosuccinimide (NBS) (4.78 g, 0.027 mol) in DMF (50 mL) is added dropwise in the dark and under argon. The resulting mixture is stirred at 0° C. for about three hours or until GC/MS shows a single peak at 415. This solution is poured into water (500 mL) and the organic solution is extracted with hexane (3×100 mL). The combined organic solutions are washed with brine (2×50 mL) and water (50 mL). After drying over MgSO4, the hexane is evaporated. The crude product is purified by column chromatography and eluted with hexane to yield the target compound (10.1 g, 90.2% yield). 1HNMR (CD2Cl2): δ 7.39 (d, 1H), 7.29 (d, 1H), 2.74 (t, 2H), 1.74-1.33 (m, 16H), 0.89 (t, 3H). 13CNMR: 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

extractionthe organic solution is extracted with hexane (3×100 mL)
washThe combined organic solutions are washed with brine (2×50 mL) and water (50 mL)
dry with materialAfter drying over MgSO4
customthe hexane is evaporated
customThe crude product is purified by column chromatography
washeluted with hexane

Sources & evidence

ORD record: ord-5132c8694e44455ea30e4f6b7d9321b8
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846855B2

Reaction notes

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