Hexane → N-(2-Bromo-5-fluorophenyl)pivalamide
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].CCCCCC>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an ice-cold solution of 2-bromo-5-fluoroaniline (50.0 g, 263.14 mmol) in DCM (400 mL) was added triethyl amine (48.0 mL, 342.10 mmol). The resulting mixture was stirred at 0° C. for 10 min followed by addition of pivaloyl chloride (36.0 mL, 289.50 mmol) then stirred at rt for 3 h. After completion of reaction (by TLC), the reaction mixture was diluted with DCM and washed with saturated solution of NaHCO3. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 1.0% EtOAc:hexane to obtain the product as an off white solid (66.0 g, 92% yield).
Workup
- stirringthen stirred at rt for 3 h
- customAfter completion of reaction (by TLC)
- washwashed with saturated solution of NaHCO3
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe crude residue was purified over 100-200 M silica-gel
Sources & evidence
- ORD record
- ord-40b1b2b87e1744fa85dbed8f2ed8857b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181234B2
Reaction notes
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