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

HRID 1516649Notes

Reaction equation

HRID 1516649 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fff3745aaf9145edb3a8b0d02119d4b2
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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