Water → 2-Bromo-3-Dodecylthiophene

HRID 888671Notes

Reaction equation

HRID 888671 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 slowly added to a solution of 3-dodecylthiophene (68 g; 0.27 mol) dissolved in DMF (110 ml). After the reaction solution was stirred for one day, 750 ml of water was added thereto. An organic material was extracted by using ethyl ether (3×300 ml), and 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
  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-d6b1d8f212a7483c997e2a070f30aa84
Source dataset
uspto-grants-2012_08
Patent number
US08247803B2

Reaction notes

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