Bromine → 2-Bromo-5-butylthiophene

HRID 256848Notes

Reaction equation

HRID 256848 reaction equation
[Br:1]Br.[CH2:3]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:4][CH2:5][CH3:6]>C(Cl)(Cl)Cl>[Br:1][C:9]1[S:8][C:7]([CH2:3][CH2:4][CH2:5][CH3:6])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 738182-n-Butylthiophene

Product 1

HCID 151718402-Bromo-5-butylthiophene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine, 5 ml (15.63 g or 0.0977 mol), was added to a solution of 15.2 g (0.108 mol) of 2-butylthiophene in 400 ml of chloroform. Following the addition, the mixture was stirred for 10 minutes at room temperature and was then washed with 10% aqueous sodium carbonate solution. The organic layer was separated, dried and evaporated and the remaining oil was distilled under high vacuum to yield a colorless oil. Nmr (CDCl3): 0.89 ppm (t, 3, J=7.5 Hz, CH3), 1.2-1.7 (m, 4, CH2CH2), 2.7 (t, 2, J=7.5 Hz, CH2), 6.47 (d, 1, J=4 Hz, C4-H), 6.78 (d, 1, J=4 Hz, C3-H).

Workup

  1. additionthe addition
  2. washwas then washed with 10% aqueous sodium carbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. distillationthe remaining oil was distilled under high vacuum
  7. customto yield a colorless oil

Sources & evidence

ORD record
ord-b11c78ce50514dd9853f251a057758fc
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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