Benzoyl Peroxide → 1-(3-(Bromomethyl)-1H-indazol-1-yl)ethanone

HRID 1377507Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:13])=[N:5]1)(=[O:3])[CH3:2].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][Br:14])=[N:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

1-Acetyl-3-methyl-1H-indazole (5.77 g, 33.1 mmol) in CCl4 (150 mL) was treated with N-bromosuccinimide (6.49 g, 36.5 mmol) and benzoyl peroxide (0.80 g, 3.3 mmol) and the mixture was heated at 70° C. for 16 h. The mixture was concentrated and the residue quickly filtered through a plug of flash silica eluting with 0→5% EtOAc in hexane to give the crude title compound contaminated with traces of dibromide and starting material. This was conveniently used directly in subsequent reactions without further purification.

Workup

concentrationThe mixture was concentrated
filtrationthe residue quickly filtered through a plug of flash silica eluting with 0→5% EtOAc in hexane

Sources & evidence

ORD record: ord-0ae690fd36394f169c56121915013db7
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665732

Reaction notes

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