Iodine → 3-Hydroxy-4,5-dichloro-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21236Notes

Reaction equation

HRID 21236 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:22])[N:5]([C:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:6]2=[O:12].CN(CCN(C)C)C.[I:31]I>C1COCC1>[OH:22][CH:4]1[C:3]2[C:7](=[C:8]([I:31])[CH:9]=[C:10]([Cl:11])[C:2]=2[Cl:1])[C:6](=[O:12])[N:5]1[C:13]([CH3:14])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:21]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684908354,5-Dichloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684887323-Hydroxy-4,5-dichloro-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4,5-dichloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (400 mg, 1.19 mmol) was dissolved in THF (16 mL), and the solution was treated with TMEDA (0.718 mL, 4.76 mmol), sec-butyl lithium-hexane solution (0.99 mol/L, 4.8 mL, 4.76 mmol) and iodine (453 mg, 1.79 mmol), followed by purification by flash column chromatography (chloroform/methanol=95/5 to 90/10) to obtain 3-hydroxy-4,5-dichloro-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (350 mg, yield 64%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=95/5 to 90/10)

Sources & evidence

ORD record
ord-0029dea66acd49b9b97bb7a19d7ddd61
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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