2-Pentylthiophene → 2-bromo-5-pentylThiophene

HRID 2121295Notes

Reaction equation

HRID 2121295 reaction equation
[CH2:1]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:11]N1C(=O)CCC1=O.C(O)(=O)C.C(Cl)(Cl)Cl>O>[Br:11][C:8]1[S:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 209952-PentylthiopheneHCID 67184N-bromobutanimideHCID 21584526Acetic acid chloroform

Product 1

HCID 113108252-bromo-5-pentylThiopheneYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-pentylthiophene, (25.2 g) N-bromosuccinimide (25.5 g) and a 1:1 chloroform acetic acid mixture (100 cm3) was heated under reflux for 1 h. Water (10 cm3) was added and the resultant solution stirred for 10 min under an atmosphere of nitrogen. The organic layer was separated off and the aqueous layer extracted with diethyl ether (2×50 cm3). The combined organic layers were washed with brine (2×100 cm3), dried (MgSO4), filtered and then evaporated down. The residue was purified by distillation (Bp 132-134° C. at 15-20 mm Hg.) to yield 32.6 g of 2-bromo-5-pentylthiophene.

Workup

  1. temperatureunder reflux for 1 h
  2. customThe organic layer was separated off
  3. extractionthe aqueous layer extracted with diethyl ether (2×50 cm3)
  4. washThe combined organic layers were washed with brine (2×100 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated down
  8. distillationThe residue was purified by distillation (Bp 132-134° C. at 15-20 mm Hg.)

Sources & evidence

ORD record
ord-76bad079f71b44409d06f5ec6a1ec022
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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