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

HRID 1515453ノート

反応式

HRID 1515453 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 70164571-(4-Bromophenyl)pyrrolidine収率 76.5%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5885fd0fa70e4550980752d5a7f6cdd6
出典データセット
uspto-grants-2012_07
特許番号
US08222424B2

反応ノート

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