Benzoyl Peroxide → HCID 12240552, compound

HRID 10226Notes

Reaction equation

HRID 10226 reaction equation
[CH3:1][C:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[S:4][CH:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][C:3]1[S:4][C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 137172Thieno(2,3-b)thiophene, 3-methyl-

Product 1

HCID 12240552HCID 12240552, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Methylthieno[2,3-b]thiophene (Step 1, 450 mg, 2.92 mmol) was dissolved in carbon tetrachloride (7 mL) under nitrogen. N-Bromosuccinimide (0.52 g, 2.92 mmol) and benzoyl peroxide (75% in water; 0.10 g, 0.29 mmol) were added and the reaction heated to reflux for 6 hours. The solvent was removed in vacuo and the residue taken up in dichloromethane then filtered onto a column of silica and eluted with isohexane to give 2-bromo-3-methylthieno[2,3-b]thiophene (0.25 g, 37%). 1H NMR (500 MHz, CDCl3) δ 7.38 (1H, d, J=5.2 Hz), 7.13 (1H, d, J=5.2 Hz), 2.34 (3H, s).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. filtrationthen filtered onto a column of silica
  5. washeluted with isohexane

Sources & evidence

ORD record
ord-012d81d01cae4b83b6deb6a888f9666b
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

Loading…