N-bromobutanimide → HCID 69300952, compound

HRID 2217923Notes

Reaction equation

HRID 2217923 reaction equation
[CH2:1]([C:13]1[S:17][C:16]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:23]N1C(=O)CCC1=O>CN(C=O)C>[Br:23][C:19]1[S:20][CH:21]=[CH:22][C:18]=1[C:16]1[S:17][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69298588HCID 69298588, compound

Product 1

HCID 69300952HCID 69300952, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

5′-Dodecyl-3,2′-bithiophene (34.5 g, 103 mmol, 1 eq) prepared above was placed in a three-necked flask equipped with a dropping funnel and a reflux tube. The atmosphere in the flask was replaced by Ar, 500 ml of dehydrated DMF was added thereto, and the mixture was stirred. The reaction solution was cooled to 0° C., and N-bromosuccinimide (19.2 g, 108 mmol, 1.05 eq) dissolved in 100 ml of dehydrated DMF in a separate vessel was added dropwise to the reaction solution. After the completion of the dropwise addition, the mixture was stirred for one hr, was brought to room temperature, and was stirred for 6 hr. The solvent was removed by evaporation, and the residue was extracted with diethyl ether, followed by washing with water until pH=7. The extract was dehydrated over Na2SO4, the solvent was removed by evaporation, and the residue was purified by chromatography on silica gel to give an objective substance 2-bromo-5′-dodecyl-3,2′-bithiophene as a light yellow liquid (which solidified a few hours after that) (about 41.5 g, yield about 97%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory). 1H-NMR (d6-DMSO, TMS/ppm): 0.86 (t, 3H, J=6.83 Hz), 1.26 (m, 18H), 1.66 (m, 2H), 2.80 (t, 2H, J=7.32 Hz), 6.83 (d, 1H, J=2.93 Hz), 7.22 (d, 1H, J=5.34 Hz), 7.32 (d, 1H, J=3.90 Hz), 7.59 (d, 1H, J=5.37 Hz).

Workup

  1. customabove was placed in a three-necked flask
  2. customequipped with a dropping funnel and a reflux tube
  3. additionwas added
  4. additionwas added dropwise to the reaction solution
  5. additionAfter the completion of the dropwise addition
  6. stirringthe mixture was stirred for one hr
  7. customwas brought to room temperature
  8. stirringwas stirred for 6 hr
  9. customThe solvent was removed by evaporation
  10. extractionthe residue was extracted with diethyl ether
  11. washby washing with water until pH=7
  12. customthe solvent was removed by evaporation
  13. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-46b831659e5f4b8d97ea731c940995d5
Source dataset
uspto-grants-2008_08
Patent number
US07408188B2

Reaction notes

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