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

HRID 1261534Notes

Reaction equation

HRID 1261534 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-4a083678f8dc4cdab5bfbae9040423b2
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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