1-Bromo-3-chloropropane → 1-Bromo-3-(3-chloropropoxy)benzene

HRID 418719Notes

Reaction equation

HRID 418719 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][Cl:15]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:12][CH2:13][CH2:14][Cl:15])[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 115633-BromophenolHCID 24758Sodium hydride

Product 1

HCID 167842551-Bromo-3-(3-chloropropoxy)benzeneYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-bromophenol (2.23 g, 12.9 mmol) in DMF (100 mL) was added, in small portions, sodium hydride (60% dispersion, 0.54 g, 13 mmol) over 30 min. 1-Bromo-3-chloropropane (2.1 g, 13 mmol) was then added dropwise and the mixture was stirred at r.t. for 24 h. It was then partitioned between ether and water, the organic phase was washed with water and brine, dried (anhydrous MgSO4) and concentrated to afford 1-bromo-3-(3-chloropropoxy)benzene (362, 2.95 g, 91% yield) (used as is with no additional purification).

Workup

  1. customIt was then partitioned between ether and water
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried (anhydrous MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f9e94eeeb0c4ce0a823ce96d3e5adbd
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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