Benzoyl Peroxide → 7-(Bromomethyl)-1-benzothiophene

HRID 348170Notes

Reaction equation

HRID 348170 reaction equation
[CH3:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 64285417-Methyl-1-benzothiophene

Product 1

HCID 107517617-(Bromomethyl)-1-benzothiopheneYield 38.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of intermediate 137, 7-methylbenzo[b]thiophene (1.0 g, 6.5 mmol) in CCl4 (20 mL) was added benzoyl peroxide (1.1 g, 4.54 mmol) followed by portionwise addition of NBS (1.15 g, 6.5 mmol). The reaction mixture stirred at reflux while irradiating with a 250 W lamp. The reaction mixture was stirred at reflux for 3 h. The solution was cooled, filtered and the solvent evaporated in vacuo. The residue was subjected to column chromatography on silica gel with hexanes as the eluent to afford the title compound (0.570 g, 33% yield): 1H NMR (400 MHz, CDCl3) δ: 7.80 (1H, dd, J=7.8, 1.7 Hz), 7.49 (1H, d, J=5.4 Hz), 7.40–7.33 (3H, m), 4.78 (2H, s). LCMS (M+H)+ m/z 209.

Workup

  1. temperatureat reflux
  2. customwhile irradiating with a 250 W lamp
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 3 h
  5. temperatureThe solution was cooled
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c04a1c25241040a18d02e55f287af6ad
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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