Azobisisobutyronitrile → 4-(bromomethyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1427908Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCCl>[Br:17][CH2:16][C:3]1[C:2]([Cl:1])=[CH:14][C:6]([C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8])=[C:5]([F:15])[CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide (0.8 g, 3.0 mmol), N-bromosuccinimide (1.6 g, 9.0 mmol) and azodiisobutyronitrile (16 mg, 0.09 mmol) in 1,2-dichloroethane (20 mL) was stirred at 90° C. for 16 hrs. The reaction was quenched with Na2S2O3 (10 mL, 10%), extracted with 1,2-dichloroethane (20 mL×3), dried over anhydrous Na2SO4, concentrated and the residue was used in next step without further purification (1.1 g, crude). LCMS (ESI) m/z: 342.0 [M+H]+.

Workup

customThe reaction was quenched with Na2S2O3 (10 mL, 10%)
extractionextracted with 1,2-dichloroethane (20 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customthe residue was used in next step without further purification (1.1 g, crude)

Sources & evidence

ORD record: ord-4dfbde27ee814d9286f78d95ecb4ef28
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933236B2

Reaction notes

Loading…