N-bromobutanimide → 3-Bromo-7-(4-methylbenzyl)-1-benzothiophene

HRID 604750Notes

Reaction equation

HRID 604750 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:15]3[S:14][CH:13]=[CH:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:17][CH:16]=3)[C:15]=2[S:14][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 670691007-(4-Methylbenzyl)benzo[b]thiophene

Product 1

HCID 670690913-Bromo-7-(4-methylbenzyl)-1-benzothiopheneYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (30 mL) solution of 7-(4-methylbenzyl)-1-benzothiophene (1.24 g, 5.20 mmol) was added with N-bromosuccinimide (1.01 g, 5.72 mmol) and stirred at room temperature for two hours. The solvent was evaporated under reduced pressure and diluted with ethyl acetate. After washed with 20 wt % sodium thiosulfate aqueous solution and brine, the organic phase was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=100:1-50:1) to obtain a colorless powdered title compound (0.92 g, 56%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washAfter washed with 20 wt % sodium thiosulfate aqueous solution and brine
  4. dry with materialthe organic phase was dried with anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=100:1-50:1)

Sources & evidence

ORD record
ord-f48401b91bce46a7bb139f0115a9f2ae
Source dataset
uspto-grants-2011_03
Patent number
US07910619B2

Reaction notes

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