Carbon Disulfide → 2-Bromo-5-benzoylthiophene

HRID 2425282Notes

Reaction equation

HRID 2425282 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.C(=S)=S>>[Br:10][C:11]1[S:12][C:13]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6348Carbon DisulfideHCID 7412Benzoyl chlorideHCID 138512-Bromothiophene

Product 1

HCID 2986042-Bromo-5-benzoylthiopheneYield 96.2%

Procedure

To a mixture of benzoyl chloride (2.81 g, 20.0 mmol) and 2-bromothiophene (3.42 g, 21.0 mmol) in carbon disulfide (120 mL) aluminum chloride (5.34 g, 40.0 mmol), was added in portions over 10 min with vigorous magnetic stirring. The reaction was next allowed to stir for 2.5 h before being quenched with 100 mL 1 M HCl(aq). The organics were separated, the aqueous layer extracted with carbon disulfide (3×50 mL), and the combined organics washed with water (3×100 mL) and dried over MgSO4. After filtration, the organics were concentrated in vacuo and the residue chromatographed on a silica gel column (hexane:ether=9:1) to yield 5.14 g (96%) of yellow crystals. mp 41-43° C.; 1H NMR (CDCl3): δ 7.84 (d, 2H, 3J=8.0 Hz), 7.62 (t, 1H, 3J=7.2 Hz), 7.52 (t, 2H, 3J=7.5 Hz), 7.40 (d, 2H, 3J=3.5 Hz), 7.15 (d, 2H, 3J=4.0 Hz).

Workup

  1. additionwas added in portions over 10 min with vigorous magnetic stirring
  2. custombefore being quenched with 100 mL 1 M HCl(aq)
  3. customThe organics were separated
  4. extractionthe aqueous layer extracted with carbon disulfide (3×50 mL)
  5. washthe combined organics washed with water (3×100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe organics were concentrated in vacuo
  9. customthe residue chromatographed on a silica gel column (hexane:ether=9:1)

Sources & evidence

ORD record
ord-a343a12cf4e74b4ca566dbc8133956a6
Source dataset
uspto-grants-2011_06
Patent number
US07964650B2

Reaction notes

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