Benzoyl Peroxide → 3-(1-Bromopropyl)-4-phenyl-1H-isochromen-1-one

HRID 634404Notes

Reaction equation

HRID 634404 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]=2[CH2:18][CH2:19][CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH:18]([C:8]1[O:9][C:10](=[O:17])[C:11]2[C:16]([C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 158933024-Phenyl-3-propyl-1H-isochromen-1-one

Product 1

HCID 1181311823-(1-Bromopropyl)-4-phenyl-1H-isochromen-1-oneYield 72.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Phenyl-3-propyl-1H-isochromen-1-one (intermediate C20.3, 107 mg, 0.405 mmol), N-bromosuccinimide (86 mg, 0.486 mmol), benzoyl peroxide (25 mg, 0.1 mmol) were reacted in CCl4 (2 mL) at 100° C. for 2 hrs. The reaction mixture was then purified on Biotage 50 g silica gel cartridge with a gradient of hexane and EtOAc to give the title compound (101 mg, 72.7%) as a yellowish oil.

Workup

  1. customThe reaction mixture was then purified on Biotage 50 g silica gel cartridge with a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-8bd182ce091445d5a69e3fddce782451
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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