Hydrochloric Acid → 1,2-bis(4-iodophenyl)ethane-1,2-dione

HRID 1176974Notes

Reaction equation

HRID 1176974 reaction equation
N1([C:10]([C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=2)=[O:11])C2C=CC=CC=2N=N1.Cl>C1COCC1>[I:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[C:10]([C:12]2[CH:13]=[CH:14][C:15]([I:18])=[CH:16][CH:17]=2)=[O:11])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 786028HCID 786028, compound

Product 1

HCID 28321531,2-bis(4-iodophenyl)ethane-1,2-dioneYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under N2, benzotriazol-1-yl-(4-iodo-phenyl)-methanone (JYC-II-056-A) (3.5 g, 10.0 mmol) dissolved in 40 mL of anhydrous THF was added to a THF solution of SmI2 (221 mL of 0.1 M solution in THF, 22.1 mmol) at room temperature. The resulting mixture turned yellow brown in 5 min. HCl (2M, 65 mL) was added and the mixture was extracted with diethyl ether several times. The combined organic layers were washed with brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was washed with MeOH to give a yellow solid (0.73 g, 31.5%). 1H NMR (300 MHz, CDCl3, δ): 7.88 (d, J=8.5 Hz, 4H), 7.64 (dt, J=8.8 Hz, 4H). HRMS-EI (m/z): [M]+ calcd for C14H8I2O2, 461.86138; found, 461.86180.

Workup

  1. extractionthe mixture was extracted with diethyl ether several times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. washThe crude product was washed with MeOH

Sources & evidence

ORD record
ord-8cdbbceae65f47caa1e90a23b66d2d2e
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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