N-bromobutanimide → 2-Bromo-3-(2-octyldodecyl)thiophene

HRID 1618063Notes

Reaction equation

HRID 1618063 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([CH:17]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][C:19]1[CH:23]=[CH:22][S:21][CH:20]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CN(C)C=O>[Br:1][C:20]1[S:21][CH:22]=[CH:23][C:19]=1[CH2:18][CH:17]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67031742HCID 67031742, compound

Product 1

HCID 670317242-Bromo-3-(2-octyldodecyl)thiopheneYield 95.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (2.58 g, 14.5 mmol) in 100 mL of dimethylformamide (DMF) was added drop-wise into a solution of 3-(2-octyldodecyl)thiophene (4.90 g, 13.2 mmol) in 300 DMF at −20° C. The mixture was stirred overnight at room temperature. Next, the DMF was removed under vacuum and 100 mL water was added. The mixture was extracted with hexane three times and the organic layers were collected. After removal of hexane, a crude product was obtained and was purified by column to afford 5.60 g of the final product in the form of colorless oil (96%). 1H NMR (CDCl3, 400 MHz, ppm) δ 7.18-7.17 (d, 1H, J=5.6 Hz), 6.76-6.75 (d, 1H, J=5.6 Hz), 2.50-2.48 (d, 2H, J=7.2 Hz), 1.64 (m, 1H), 1.30-1.25 (br, 32H), 0.90-0.87 (t, 6H).

Workup

  1. customNext, the DMF was removed under vacuum and 100 mL water
  2. additionwas added
  3. extractionThe mixture was extracted with hexane three times
  4. customthe organic layers were collected
  5. customAfter removal of hexane
  6. customa crude product was obtained
  7. customwas purified by column

Sources & evidence

ORD record
ord-a28c4e5427ec45179dde153a89c32014
Source dataset
uspto-grants-2014_07
Patent number
US08765968B2

Reaction notes

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