Triethylamine → 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.Cl[CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22].CC(C)([O-])C.[K+].C([O-])([O-])=O.[Na+].[Na+]>O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:18][CH2:19][CH2:20][C:21]2=[O:22])=[CH:4][C:3]=1[CH3:9]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
A stirred solution of 4-bromo-3-methylaniline (50.3 g, 0.27 mole) and triethylamine (41.1 ml, 0.30 mole) in THE (250 ml) at 0° C. under argon was treated dropwise with 4-chlorobutyryl chloride (33.4 ml, 0.30 mole). The mixture was stirred for 1 hour at 0-5° C., then potassium t-butoxide (82.5 g, 0.74 mole) was added portionwise over 20 minutes, maintaining temperature below 25° C. The reaction mixture was stirred at 25° C. for a further 2.5 hrs, then treated with water (100 ml), followed after 0.25 hrs with 10% aqueous Na2CO3 solution and then extracted with ethyl acetate. The extract was washed with water, 5M HCl acid, then brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound as a pale yellow solid (61.6 g, 89%).
Workup
- temperaturemaintaining temperature below 25° C
- stirringThe reaction mixture was stirred at 25° C. for a further 2.5 hrs
- extractionextracted with ethyl acetate
- washThe extract was washed with water, 5M HCl acid
- dry with materialbrine, dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-355acfbd772e4d3ab98584800100e01f
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06100272
Reaction notes
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