1,3-Dibromopropane → Methyl 2-[4-(3-bromopropoxy)phenyl]acetate

HRID 1532141Notes

Reaction equation

HRID 1532141 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:13][CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10803177Methyl 2-[4-(3-bromopropoxy)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-hydroxyphenylacetate (20.0 g, 0.12 mol), 1,3-dibromopropane (97.2 g, 0.48 mol) and cesium carbonate (43.1 g, 0.13 mol) in dry DMF (250 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with methylene chloride/hexane (2:1) to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.2N HCl
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. customevaporated to an oil which
  6. customwas chromatographed over silica gel with methylene chloride/hexane (2:1)

Sources & evidence

ORD record
ord-862e507c494f4c9f85bf4aded01bbe11
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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