Acetic Acid → 2-Bromo-3-(4-bromobutyl)thiophene

HRID 85347Notes

Reaction equation

HRID 85347 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.C(O)(=O)C.C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)Cl>[Br:22][C:7]1[S:8][CH:9]=[CH:10][C:6]=1[CH2:5][CH2:4][CH2:3][CH2:2][Br:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 145911113-(4-Bromobutyl)thiophene

Product 1

HCID 668235992-Bromo-3-(4-bromobutyl)thiopheneYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(4-bromobutyl)thiophene (8 g, 36.5 mmol) was dissolved in 250 ml CHCl3, and glacial acetic acid (250 ml) was added in the dark. NBS (6.5 g, 36.5 mmol) was added, and the mixture was stirred for 20 minutes at room temperature in the dark. The reaction mixture was washed with water, saturated NaHCO3, dried over magnesium sulfate and the solvent was removed under vacuum. Purification by column chromatography afforded the title compound (7.4 g, 68% yield) as a light yellow oil. 1H-NMR (ppm, CDCl3): 1.71-1.77 (2H, m), 1.85-1.89 (2H, m), 2.6 (2H, t, J=7.44 Hz), 3.43 (2H, t, J=7.32 Hz), 6.78 (1H, d, J=5.6 Hz), 7.19 (1H, d, J=5.6 Hz); 13C-NMR (ppm, CDCl3): 27.5, 29.4, 32.9, 33.9, 109.2, 125.5, 128.4, 141.8; GC-MS (m/z): 295.89.

Workup

  1. washThe reaction mixture was washed with water, saturated NaHCO3
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was removed under vacuum
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-cc53a279739f4d41b817bea68080df63
Source dataset
uspto-grants-2014_09
Patent number
US08847068B2

Reaction notes

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