Water → 5-Bromo-4,4'-didodecyl-2,2'-bithiophene

HRID 2078762Notes

Reaction equation

HRID 2078762 reaction equation
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:22]=2)[S:16][CH:17]=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:42])C(=O)C1.O>C(Cl)(Cl)Cl.CC(O)=O>[Br:42][C:20]1[S:19][C:18]([C:15]2[S:16][CH:17]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=2)=[CH:22][C:21]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 219172654,4'-Didodecyl-2,2'-bithiophene

Product 1

HCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneYield 85%

Reagents, catalysts & solvents 1

HCID 21584526Acetic acid chloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4,4′-didodecyl-2,2′-bithiophene (0.100 g, 0.199 mmol) in CHCl3/HOAc (1:1) (Vt=2.0 mL) at 0° C. was added N-bromosuccimide (NBS, 35.7 mg, 0.199 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 filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexanes) to provide 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A) as a colorless oil (98.0 mg, 85% yield). 1H NMR (CDCl3): δ 0.84-1.54 (m, 46H), 2.57 (m, 4H), 6.81 (s, 1H), 6.84 (s, 1H), 6.94 (s, 1H).

Workup

  1. extractionextracted with chloroform (3×50.0 mL)
  2. washThe combined organic phases were washed with water (50.0 mL), NaOH solution
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration through Celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-2a92a1e3edf1455490830238d1690034
Source dataset
uspto-grants-2011_04
Patent number
US07928249B2

Reaction notes

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