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

HRID 1810182노트

반응식

HRID 1810182 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 70164571-(4-Bromophenyl)pyrrolidine수율 76.5%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c4c93740c3f43bd840941cd20246053
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362063B2

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