Sodium hydride → 3-(2-Bromo-4-chlorophenoxy)-1-isopropylpyrrolidine

HRID 1245863Notes

Reaction equation

HRID 1245863 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11].CS(O[CH:17]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18]1)(=O)=O>CC(N(C)C)=O>[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH:17]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696702-Bromo-4-chlorophenolHCID 219143101-Isopropylpyrrolidin-3-yl methanesulphonate

Product 1

HCID 219142883-(2-Bromo-4-chlorophenoxy)-1-isopropylpyrrolidineYield 93%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
90 °C

Procedure

Sodium hydride (0.43 g, 60% dispersion in oil) was added portionwise to a stirred solution of 2-bromo-4-chlorophenol (2.1 g) in dimethylacetamide (15 ml). After stirring for 15 minutes, a solution of 1-isopropylpyrrolidin-3-yl methanesulphonate (15 mmol) in dimethylacetamide (15 ml) was added portionwise and the resulting mixture was heated at 90° C. for 18 h. The solvent was evaporated and the residue dissolved in ethyl acetate/water. The solvent phase was washed twice with brine and then dried and evaporated to an oil. Purification was achieved using silica chromatography eluting with dichloromethane/methanol mixtures. This gave the title compound (3.0 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate/water
  3. washThe solvent phase was washed twice with brine
  4. customdried
  5. customevaporated to an oil
  6. customPurification
  7. washeluting with dichloromethane/methanol mixtures

Sources & evidence

ORD record
ord-d51ece9354124382861547b48d44fb45
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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