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

HRID 540967Notes

Reaction equation

HRID 540967 reaction equation
[CH2:1]([CH:3]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O>C1COCC1>[Br:14][C:6]1[S:7][CH:8]=[CH:9][C:5]=1[CH2:4][CH:3]([CH2:1][CH3:2])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 144195433-(2-Ethylhexyl)thiophene

Product 1

HCID 580982912-Bromo-3-(2-ethylhexyl)thiopheneYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 150 mL of THF solution of (9-4) (5.3 g, 26.9 mmol), N-bromosuccinimide (4.8 g, 26.9 mmol) was added portionwise at 0° C. and the mixture was stirred at 0° C. overnight. The organic fraction was extracted with water and CHCl3, washed with NaHCO3 aq., and dried over anhydrous Mg2SO4. The crude product was further purified by column chromatography using hexane as the eluent give (9-5) as a colourless liquid (6.9 g, 93%). 1H NMR (CDCl3, 300 MHz, ppm): 7.18 (d, 1H, J=5.7 Hz), 6.76 (d, 1H, J=5.7 Hz), 2.50 (d, 2H, J=7.2 Hz), 1.55-1.62 (m, 1H), 1.25-1.34 (m, 8H), 0.85-0.90 (m, 6H).

Workup

  1. extractionThe organic fraction was extracted with water and CHCl3
  2. washwashed with NaHCO3 aq.
  3. dry with materialdried over anhydrous Mg2SO4
  4. customThe crude product was further purified by column chromatography

Sources & evidence

ORD record
ord-4f63526b10204d5d81cc9da9c24307db
Source dataset
uspto-grants-2014_10
Patent number
US08871884B2

Reaction notes

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