1,4-Dibromobutane → 1-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidine

HRID 1158168ノート

反応式

HRID 1158168 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Br.[Cl-].[NH4+]>O1CCCC1.CS(C)=O>[Br:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

参加物

7

反応物 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

生成物 1

HCID 666722611-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidine収率 52%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5.7 g (0.14 mol) of sodium hydride are suspended in 200 mL of tetrahydrofuran. 10 g (44 mmol) of 4-bromo-2-tert-butylaniline are added, along with 200 mL of dimethyl sulfoxide, added slowly. The mixture turns blue and, after 30 minutes, 13 mL (0.14 mol) of 1,4-dibromobutane are added and the reaction medium is stirred at room temperature for 13 hours. The reaction medium is then poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is then washed twice with water, dried and then concentrated to dryness. The residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 6.4 g of 1-(4-bromo-2-tert-butylphenyl)pyrrolidine are obtained (yield=52%) in the form of a thick yellow oil.

後処理

  1. additionadded slowly
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed twice with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-242455e74f32427089eca1c5b16b0d2f
出典データセット
uspto-grants-2010_10
特許番号
US07807708B2

反応ノート

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