2-Bromophenol → 3-(2-Bromophenoxy)-1-isopropylpyrrolidine

HRID 1245858Notes

Reaction equation

HRID 1245858 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].CS(O[CH:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17]1)(=O)=O>CC(N(C)C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17]1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 24758Sodium hydrideHCID 219143101-Isopropylpyrrolidin-3-yl methanesulphonate

Product 1

HCID 219142903-(2-Bromophenoxy)-1-isopropylpyrrolidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of 2-bromophenol (2.6 g) in dimethylacetamide (20 ml) was added sodium hydride (640 mg) portionwise. A solution of 1-isopropylpyrrolidin-3-yl methanesulphonate [Example 134 (c)] in dimethylacetamide (20 ml) was added and the mixture was heated to 150° C. for 18 h. The mixture was allowed to cool and partitioned between water and dichloromethane. The organic phase was extracted with 2N aqueous hydrochloric acid which was then neutralised and extracted with dichloromethane. The extracts were dried (MgSO4), the solvent removed under vacuum and the product purified by silica chromatography using dichloromethane/aqueous ammonia/methanol mixtures to yield the title compound as a brown oil (496 mg).

Workup

  1. temperatureto cool
  2. custompartitioned between water and dichloromethane
  3. extractionThe organic phase was extracted with 2N aqueous hydrochloric acid which
  4. extractionextracted with dichloromethane
  5. dry with materialThe extracts were dried (MgSO4)
  6. customthe solvent removed under vacuum
  7. customthe product purified by silica chromatography

Sources & evidence

ORD record
ord-7c5dea4ce75d401f9f11baa818f67ab6
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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