N-bromobutanimide → 2-Bromo-3-n-octylthiophene

HRID 2410241Notes

Reaction equation

HRID 2410241 reaction equation
[CH2:1]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.O>[Br:21][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5668523-Octylthiophene2×

Product 1

HCID 107548542-Bromo-3-n-octylthiopheneYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

3-Octylthiophene (45 g) was dissolved in DMF (327 mL). NBS (40.75 g) was dissolved in DMF (300 mL) and was subsequently added dropped to the 3-octylthiophene solution at room temperature under the darkness. The reaction mixture was subsequently stirred at room temperature overnight, slowly diluted with water (800 mL) and extracted with diethyl ether (3×300 mL). The combined organic extracts were subsequently washed with brine (2×200 mL) and water (200 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated. Vacuum distillation of the crude residue afforded the title compound as a colorless liquid (56.0 g, yield: 89%): 1H NMR (300 MHz, CDCl3, ppm) δ: 7.15-7.13(d, 1H), 6.78-6.76(d, 1H), 2.57-2.52(t, 2H), 1.59-1.54(m, 2H), 1.29-1.27(m, 10H), 0.90-0.86(t, 3H).

Workup

  1. additionwas subsequently added
  2. extractionextracted with diethyl ether (3×300 mL)
  3. washThe combined organic extracts were subsequently washed with brine (2×200 mL) and water (200 mL)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. distillationVacuum distillation of the crude residue

Sources & evidence

ORD record
ord-2f8a0804a4444469bd13c8c3355d8634
Source dataset
uspto-grants-2014_08
Patent number
US08816035B2

Reaction notes

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