Water → 2-Bromo-3-Dodecylthiophene

HRID 1874016Notes

Reaction equation

HRID 1874016 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:21]1[CH:25]=[CH:24][S:23][CH:22]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[Br:1][C:22]1[S:23][CH:24]=[CH:25][C:21]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 27336553-Dodecylthiophene

Product 1

HCID 104268162-Bromo-3-DodecylthiopheneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (NBS) (48 g; 0.27 mol) dissolved in DMF (160 ml) was added dropwise to 3-dodecylthiophene (68 g; 0.27 mol) dissolved in DMF (110 ml). The reaction solution was stirred for one day, 750 ml of water was added thereto. An organic material was extracted from ethyl ether (3×300 ml), washed with brine and water, and then the residual moisture was removed over anhydrous magnesium sulfate. After removing the solvent, the residue was distilled off under reduced pressure at 125° C./˜5 mmHg to obtain a product (84.85 g, yield of 94%).

Workup

  1. extractionAn organic material was extracted from ethyl ether (3×300 ml)
  2. washwashed with brine and water
  3. customthe residual moisture was removed over anhydrous magnesium sulfate
  4. customAfter removing the solvent
  5. distillationthe residue was distilled off under reduced pressure at 125° C./˜5 mmHg

Sources & evidence

ORD record
ord-7247a59a23094ea8add432487c0d1691
Source dataset
uspto-grants-2012_11
Patent number
US08304555B2

Reaction notes

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