Water → 2-Bromo-3-Dodecylthiophene

HRID 2078757Notes

Reaction equation

HRID 2078757 reaction equation
[CH2:1]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1C(=O)N([Br:25])C(=O)C1.O>C(Cl)(Cl)Cl.CC(O)=O>[Br:25][C:14]1[S:15][CH:16]=[CH:17][C:13]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 27336553-Dodecylthiophene

Product 1

HCID 104268162-Bromo-3-DodecylthiopheneYield 93%

Reagents, catalysts & solvents 1

HCID 21584526Acetic acid chloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-dodecylthiophene (5.00 g, 19.8 mmol) in CHCl3/HOAc (1:1) (Vt=20.0 mL) at 0° C. was added NBS (3.52 g, 19.8 mmol) in portions over a period of 45 minutes. The reaction mixture was stirred for 1 hour at 0° C., and overnight at room temperature. The reaction mixture was poured into water (50.0 mL) and extracted with chloroform (3×50.0 mL). The combined organic phases were washed with water (50.0 mL), NaOH solution, and dried over MgSO4. After filtration through Celite, the chloroform was removed in vacuo, and the product was obtained as a colorless oil (6.05 g, 93% yield). 1H NMR (CDCl3): δ 0.84-1.54 (m, 23H), 2.53 (t, 2H), 6.76 (d, 1H, J=4.5 Hz), 7.15 (d, 1H, J=4.5 Hz).

Workup

  1. customovernight
  2. customat room temperature
  3. extractionextracted with chloroform (3×50.0 mL)
  4. washThe combined organic phases were washed with water (50.0 mL), NaOH solution
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration through Celite
  7. customthe chloroform was removed in vacuo

Sources & evidence

ORD record
ord-73a7cf8481b54d4caff3f995649e8e30
Source dataset
uspto-grants-2011_04
Patent number
US07928249B2

Reaction notes

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