N,N,N',N'-Tetramethylethylenediamine → 3-Hydroxy-7-bromo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21232

Reaction equation

HRID 21232 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13].CN(CCN(C)C)C.[Br:29]C(Cl)(Cl)C(Cl)(Cl)Br>C1COCC1>[OH:11][CH:4]1[C:5]2[C:10](=[C:9]([Br:29])[CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C:12]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 109892423-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684926173-Hydroxy-7-bromo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.00 g, 7.48 mmol) was dissolved in THF (80 mL), and the solution was treated with TMEDA (2.50 mL, 16.5 mmol), sec-butyl lithium-hexane solution (0.99 mol/L, 16.6 mL, 16.5 mmol) and 1,2-dibromotetrachloroethane (2.92 g, 8.98 mmol), followed by purification by flash column chromatography (chloroform/methanol=95/5 to 90/10) to obtain 3-hydroxy-7-bromo-2-(1-methyl-1-phenylethyl)isoindolinone (2.20 g, yield 85%).

Workup

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

Sources & evidence

ORD record
ord-b1d5cfde3bb044bdadcdf25d1647a3a7
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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