N-bromobutanimide → HCID 67453822, compound

HRID 628232Notes

Reaction equation

HRID 628232 reaction equation
[CH2:1]([CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1C(=O)N([Br:29])C(=O)C1.C(=O)([O-])O.[Na+]>C1COCC1>[Br:29][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[CH2:8][CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 674565533-(2-Hexyldecyl)thiophene

Product 1

HCID 67453822HCID 67453822, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 3-(2-hexyldecyl)thiophene (10 g, 32.4 mmol) and THF (100 ml) were added and then cooled to 0° C. NBS (5.75 g, 32.4 mmol) was slowly added, and the temperature was increased to room temperature. The mixture was then stirred overnight. Then, a saturated sodium hydrogen carbonate aqueous solution (50 ml) was added to the reaction solution, followed by extraction with hexane, and an organic layer was washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solvent was distilled off under reduced pressure. By separating and purifying the obtained reaction mixture by silica gel column chromatography in which hexane was used as a mobile phase, 2-bromo-3-(2-hexyldecyl)thiophene (A2) was obtained as clear oil (12.4 g, 99% yield). The product (A2) obtained was identified using a 1H-NMR method. 1H-NMR (400 MHZ, CDCl3, TMS) δ 7.17 (d, J=5.4 Hz, 1 H), 6.75 (d, J=5.4 Hz, 1 H), 2.49 (d, J=7.0 Hz, 2 H), 1.25 (m, 25 H), 0.88 (m, 6 H)

Workup

  1. temperaturethe temperature was increased to room temperature
  2. extractionfollowed by extraction with hexane
  3. washan organic layer was washed with a saturated saline solution and water
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationafter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customBy separating
  8. custompurifying
  9. customthe obtained reaction mixture by silica gel column chromatography in which hexane

Sources & evidence

ORD record
ord-a1a1aef72fdb406b932d015a79aadc0e
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

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