Azobisisobutyronitrile → 2-Bromo-2-(4-bromo-2-fluorophenyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([F:12])[CH:3]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:12])[C:9]([NH2:11])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a suspension of 2-(4-bromo-2-fluorophenyl)acetamide (29.7 mmol) and N-bromosuccinimide (37.2 mmol) in anhydrous carbon tetrachloride (85 ml) was added 2,2′-azobis(2-methylpropionitrile) (1.487 mmol). The reaction mixture was heated at 85° C. for 4 days. The resulting suspension was concentrated in vacuo and the residue was taken into brine and then extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and decolorizing charcoal, filtered through a short pad of celite, and evaporated to a crude residue. Purification of the residue by flash chromatography (30% ethyl acetate in hexanes) afforded the title product (3.60 g, 38% yield) as a cream-colored solid. MS(ES)+m/e 310.1, 312.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.79 (s, 1 H) 7.48 (dd, J=8.59, 1.77 Hz, 1 H) 7.59 (br. s., 1 H) 7.61 (dd, J=9.85, 2.02 Hz, 1 H) 7.70 (t, J=8.21 Hz, 1 H) 7.91 (br. s., 1 H).
Workup
- concentrationThe resulting suspension was concentrated in vacuo
- extractionextracted with ethyl acetate
- dry with materialThe combined extracts were dried over sodium sulfate
- filtrationfiltered through a short pad of celite
- customevaporated to a crude residue
- customPurification of the residue by flash chromatography (30% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-bb53bd4105f544e08f0a9ebd8b11ec0e
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09084794B2
Reaction notes
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