1,3-Dibromobenzene → HCID 57421404, compound

HRID 641931Notes

Reaction equation

HRID 641931 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH3:9][O:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1.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+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:8][C:4]1[CH:3]=[C:2]([N:13]2[CH2:14][CH2:15][CH:11]([O:10][CH3:9])[CH2:12]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 113554473-Methoxypyrrolidine

Product 1

HCID 57421404HCID 57421404, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Into a 250 mL 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dibromobenzene (11.9 g, 50.42 mmol) in toluene (100 mL). To this was added 3-methoxypyrrolidine (6.1 g, 60.40 mmol). Addition of Pd(OAc)2 (113 mg, 0.50 mmol) was next. This was followed by the addition of BINAP (940 mg, 1.51 mmol). To the mixture was added Cs2CO3 (40.9 g, 125.54 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 1:30 ethyl acetate/petroleum ether solvent system. This resulted in 8.3 g (64.3%) of 1-(3-bromophenyl)-3-methoxypyrrolidine as yellow oil.

Workup

  1. customInto a 250 mL 3-necked round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customto react
  4. temperaturewas maintained
  5. temperatureat reflux in a bath of oil
  6. filtrationA filtration
  7. concentrationThe filtrate was concentrated by evaporation under vacuum
  8. customa rotary evaporator
  9. customThe residue was purified
  10. washby eluting through a column with a 1:30 ethyl acetate/petroleum ether solvent system
  11. customThis resulted in 8.3 g (64.3%) of 1-(3-bromophenyl)-3-methoxypyrrolidine as yellow oil

Sources & evidence

ORD record
ord-b7088b9d74e94f088bd4218b8c70b943
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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