Water → 2-Bromo-3-hexylthiophene

HRID 2093121Notes

Reaction equation

HRID 2093121 reaction equation
[CH2:1]([C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:12]N1C(=O)CCC1=O.O.CCCCCC>CN(C)C=O>[Br:12][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 67184N-bromobutanimideHCID 5668493-Hexylthiophene

Product 1

HCID 109601412-Bromo-3-hexylthiopheneYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 g of 3-n-hexylthiophene was dissolved in 400 ml of dimethylformamide, and to this, 50 g of N-bromosuccinimide was added. The resulting solution was stirred at room temperature for 4 hours under a nitrogen atmosphere. 200 ml of water and 200 ml of hexane were added to the resulting solution to separate the organic layer. The organic layer was washed with 200 ml of water and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure with a rotary evaporator to obtain 60 g of 2-bromo-3-n-hexylthiophene.

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with 200 ml of water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure with a rotary evaporator

Sources & evidence

ORD record
ord-87118d8606004ecca0f36e94f54cf5db
Source dataset
uspto-grants-2013_05
Patent number
US08441002B2

Reaction notes

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