Water → 4-Methanesulfonyloxy-5-methoxy-7-iodoisoindolinone

HRID 21272Notes

Reaction equation

HRID 21272 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:14].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>ClCCl.CCCCCC>[CH3:22][S:23]([O:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:14])(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684899574-Hydroxy-5-methoxy-7-iodoisoindolinone

Product 1

HCID 768469524-Methanesulfonyloxy-5-methoxy-7-iodoisoindolinoneYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In a similar manner to Step 1 of Example 289, 4-hydroxy-5-methoxy-7-iodoisoindolinone (250 mg, 0.819 mmol) was dissolved in dichloromethane (5 mL), and the solution was treated with triethylamine (0.685 mL, 4.91 mmol) and methanesulfonyl chloride (0.190 mL, 2.45 mmol). The mixture was added with water and hexane. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-methanesulfonyloxy-5-methoxy-7-iodoisoindolinone (284 mg, yield 91%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-cbbb3d89882d47bba3b2c15cb8eb95f0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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