1-Bromo-4-iodobenzene → 1-(4-Bromophenyl)pyrrolidine

HRID 1515453Notes

Reaction equation

HRID 1515453 reaction equation
CC(C)([O-])C.[Na+].I[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.C1(C)C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 31268PyrrolidineHCID 23676156Sodium t-butoxide

Product 1

HCID 70164571-(4-Bromophenyl)pyrrolidineYield 76.5%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A oven-dried 50 mL of round bottom flask is charged with Pd2(dba)3 (116 mg, 0.13 mmol), BINAP (158 mg, 0.25 mmol), and sodium tert-butoxide (916 mg, 9.54 mmol). The flask is evacuated and backfilled with argon. Degassed toluene (5 mL), 1-iodo-4-bromobenzene (1.8 g, 6.36 mmol), pyrrolidine (542 mg, 7.63 mmol) are then added. The mixture is heated at 80° C. until the starting aryl iodide is completed consumed judged by LC-MS analysis. The mixture is diluted with ethyl acetate, filtered through Celite, and concentrated in vacuo. The crude product is purified by flash chromatography to give 1.1 g of product as light brown solid. 1H NMR (400 MHz, CDCl3): δ 2.00 (t, 4H, J=4 Hz), 3.24 (t, 4H, J=4 Hz), 6.42 (d, 2H, J=8 Hz), 7.29 (d, 2H, J=8 Hz).

Workup

  1. customThe flask is evacuated
  2. customis completed consumed
  3. additionThe mixture is diluted with ethyl acetate
  4. filtrationfiltered through Celite
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-5885fd0fa70e4550980752d5a7f6cdd6
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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