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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 270682Generated: October 29, 2026

Thionyl Chloride → 6-Bromo-3-chloro-2-(4-trifluoromethylphenyl)-2H-indazole

https://huagongshe.com/reaction/270682

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant2-Azido-4-bromo-N-(4-trifluoromethylphenyl)-benzamideHCID 86051549—
Product6-Bromo-3-chloro-2-(4-trifluoromethylphenyl)-2H-indazoleHCID 6920161785%

Reaction Steps

A solution of the product of Step 2 (3 g, 0.0078 mol) in SOCl2 (15 mL) was heated at reflux for 24 h. The mixture was then concentrated and the residue partitioned between ether (3×20 mL) and Na2CO3 solution (10 mL). The organic phase was separated, dried (MgSO4) and concentrated to give 2.5 g (85% yield) of product as a tan powder. 1H NMR (360 MHz, CDCl3): 7.25 (1H, d, J 8.9 Hz), 7.37 (1H, d, 8.9 Hz), 7.80-7.95 (5H, m).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07449585B2
Source datasetuspto-grants-2008_11
ORD IDord-33609ee6604244e9b136f26b5ecde58c
Source noteuspto-grants-2008_11