Water → 4-Methanesulfonyloxy-7-iodoisoindolinone

HRID 21184Notes

Reaction equation

HRID 21184 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>ClCCl.CCCCCC>[CH3:20][S:21]([O:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12])(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 684897404-Hydroxy-7-iodoisoindolinone

Product 1

HCID 768469514-Methanesulfonyloxy-7-iodoisoindolinoneYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

4-Hydroxy-7-iodoisoindolinone (400 mg, 1.45 mmol) was dissolved in dichloromethane (10 mL), and the solution was added with triethylamine (0.808 mL, 5.80 mmol) and added with methanesulfonyl chloride (0.224 mL, 2.89 mmol) at 0° C., followed by stirring at room temperature for 2 hours. The mixture was added with methanesulfonyl chloride (0.112 mL, 1.45 mmol) at 0° C., followed by stirring at room temperature for 2 hours. The reaction mixture was added with water and hexane. The precipitated solid was collected by filtration, washed with hexane and water and then dried under reduced pressure to obtain 4-methanesulfonyloxy-7-iodoisoindolinone (353 mg, yield 69%).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with hexane and water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bff9d0ec2de84041a15174b5aca74dde
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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