Iodine → HCID 57517766, compound

HRID 601769Notes

Reaction equation

HRID 601769 reaction equation
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8].II.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22].[Cl-].[NH4+]>C(OCC)C.C1COCC1>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

8

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 843142-Bromo-3-methylthiopheneHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

Product 1

HCID 57517766HCID 57517766, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
21 °C

Procedure

Magnesium turnings (6.8 g, 0.27 mmol) are introduced into diethyl ether (30 ml), and, while stirring, a solution of 2-bromo-3-methyl-thiophene (50 g, 0.282 mol) in diethyl ether (100 ml) is added dropwise. The reaction can be initiated if necessary by adding iodine crystals. During the addition, the reaction mixture should boil gently. After the addition, the mixture was stirred at room temperature for 1 hour. A suspension of 5-chloroisatin (19 g, 0.105 mol) in THF (200 ml) was added to the Grignard solution while cooling slightly (temperature 18-24° C.) and the mixture was stirred at room temperature for 30 min. The reaction mixture was stirred into ammonium chloride solution and extracted several times with ethyl acetate. The combined organic phases were washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was stirred with diethyl ether. The resulting precipitate was filtered off, washed with diethyl ether and dried. 26 g of the desired intermediate were obtained.

Workup

  1. customThe reaction
  2. additionDuring the addition
  3. additionAfter the addition
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. additionwas added to the Grignard solution
  6. stirringthe mixture was stirred at room temperature for 30 min
  7. extractionextracted several times with ethyl acetate
  8. washThe combined organic phases were washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. stirringThe residue was stirred with diethyl ether
  12. filtrationThe resulting precipitate was filtered off
  13. washwashed with diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-7049436f2582480e993b86f8275930f4
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

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