Bromobenzene → 1-Phenylpyrrolidin-2-one

HRID 641940Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:2]1([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 150 mL sealed tube purged and maintained with an atmosphere of nitrogen, was placed 1-bromobenzene (4 g, 25.48 mmol). To this was added pyrrolidin-2-one (2.18 g, 25.65 mmol). Addition of Pd(OAc)2 (57 mg, 0.25 mmol) was next. This was followed by the addition of BINAP (240 mg, 0.39 mmol). This was followed by the addition of Cs2CO3 (12.5 g, 38.34=mol). To the mixture was added toluene (50 mL). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 1:10 ethyl acetate/petroleum ether solvent system. This resulted in 1 g (24%) of 1-phenylpyrrolidin-2-one as yellow oil.

Workup

customInto a 150 mL sealed tube
custompurged
temperaturemaintained with an atmosphere of nitrogen
customto react
concentrationThe mixture was concentrated by evaporation under vacuum
customa rotary evaporator
customThe residue was purified
washby eluting through a column with a 1:10 ethyl acetate/petroleum ether solvent system
customThis resulted in 1 g (24%) of 1-phenylpyrrolidin-2-one as yellow oil

Sources & evidence

ORD record: ord-3fd9d4b6be744258b6a93e1ded9fd176
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696229B2

Reaction notes

Loading…