Iodine → HCID 58955089, compound

HRID 1990980Notes

Reaction equation

HRID 1990980 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[I-].[K+].II>C(O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5][NH:6]2

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 7969ThiophenolHCID 6764944-Bromoindole

Product 1

HCID 58955089HCID 58955089, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A stirred solution of 4-bromo-1H-indole (4.69 g, 23.9 mmol) in ethanol (110 mL) was added thiophenol (2.46 mL, 23.9 mmol). A solution of potassium iodide (3.97 g, 24 mmol) and iodine (6.07 g, 24 mmol) dissolved in water (5 mL) and ethanol (5 mL) is added over 5 minutes and the reaction was heated at 45° C. for 12 hours. The brown reaction is concentrated in vacuo to a dark brown oil and diluted with ethyl acetate (250 mL). The organic layer is washed with water (80 mL×2), saturated Na2S2O3 (80 mL), and brine (80 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (20-30% ethyl acetate/petroleum ether) gave the title compound as a white solid (7.24 g, 99.5%). Mp: 137-139° C. MS (ES−): 302 (M−H).

Workup

  1. customThe brown reaction
  2. concentrationis concentrated in vacuo to a dark brown oil
  3. additiondiluted with ethyl acetate (250 mL)
  4. washThe organic layer is washed with water (80 mL×2), saturated Na2S2O3 (80 mL), and brine (80 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (20-30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5d42cb827216477b984dc217dd79842b
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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