Benzoyl Peroxide → 6-Bromo-4-(bromomethyl)-2-(phenylsulfonyl)isoquinolin-1(2H)-one

HRID 906415Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]=[C:5]2[CH3:22].[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14])[CH:6]=[C:5]2[CH2:22][Br:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-bromo-4-methyl-2-(phenylsulfonyl)isoquinolin-1(2H)-one (Example 11c, 4.55 g) in benzene (40 mL) was treated with N-bromosuccinimide (3.00 g) and benzoyl peroxide (0.291 g) under nitrogen. The resulting solution was heated at 80° C. for 3 h. The cooled reaction mixture was evaporated to dryness. Purification (SiO2 chromatography, elution with 60% DCM in isohexane) afforded the subtitle compound (3.40 g) as a white solid.

Workup

customThe cooled reaction mixture
customwas evaporated to dryness
customPurification (SiO2 chromatography, elution with 60% DCM in isohexane)

Sources & evidence

ORD record: ord-b8345cd40ae14166a5588aa5a0c7a182
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012980B2

Reaction notes

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