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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1896947Generated: October 31, 2026

Azobisisobutyronitrile → 3-Bromo-6-(trifluoromethyl)phthalide

https://huagongshe.com/reaction/1896947

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAzobisisobutyronitrileHCID 6547—
ReactantN-bromobutanimideHCID 67184—
Reactant6-(Trifluoromethyl)isobenzofuran-1(3H)-oneHCID 11074441—
SolventCarbon TetrachlorideHCID 5943—
Product3-Bromo-6-(trifluoromethyl)phthalideHCID 58562867—

Reaction Conditions

Temperature65 °C

Reaction Steps

Into a 50 mL round-bottom flask, was placed a solution of 6-(trifluoromethyl)isobenzofuran-1(3H)-one (prepared as described in the previous step, 5.5 g, 27.23 mmol, 1.00 equiv) in CCl4 (10 mL), NBS (5.8 g, 32.58 mmol, 1.20 equiv) and AIBN (0.45 g, 0.10 equiv). The reaction mixture was stirred for 3 h at 65° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in 100 mL of ethyl acetate, washed with 60 mL of brine, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08518969B2
Source datasetuspto-grants-2013_08
ORD IDord-6f27f8b3c9ba4c56b153013f61dbca0d
Source noteuspto-grants-2013_08