Trifluoroacetic acid → 7-Bromo-2,3-dihydro-1H-isoindol-1-one

HRID 21233Notes

Reaction equation

HRID 21233 reaction equation
O[CH:2]1[C:10]2[C:5](=[C:6]([Br:11])[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:12])[N:3]1C(C)(C1C=CC=CC=1)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[Br:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[C:4](=[O:12])[NH:3][CH2:2]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684926173-Hydroxy-7-bromo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 153153107-Bromo-2,3-dihydro-1H-isoindol-1-oneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 3-hydroxy-7-bromo-2-(1-methyl-1-phenylethyl)isoindolinone (3.00 mg, 0.867 mmol) was dissolved in nitromethane (12 mL), and the solution was treated with trifluoroacetic acid (0.668 mL, 8.67 mmol) and triethylsilane (0.277 mL, 1.73 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1) to obtain 7-bromoisoindolinone (140 mg, yield 76%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1)

Sources & evidence

ORD record
ord-4fcc87ab73384d389e5300a85fa8ac24
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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