1,3-Dibromopropane → HCID 18414623, compound

HRID 991580Notes

Reaction equation

HRID 991580 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:15][CH2:16][CH2:17][CH2:18][O:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 18414632HCID 18414632, compound

Product 1

HCID 18414623HCID 18414623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 3-hydroxymandelate (10.0 g), 1,3-dibromopropane (41.16 g) and potassium carbonate (8.08 g) in dry DMF (150 mL) was stirred at 40° C. overnight. The reaction mixture was partitioned between ethyl acetate and 1.0 N HCl. The organic layer was washed twice with water, once with brine and then dried over sodium sulfate. The organic layer was then filtered and the solvent removed in vacuo. The resulting oil was chromatographed on silica gel, using a gradient of 100% hexane to methylene chloride-hexane to yield the titled compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1.0 N HCl
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was then filtered
  5. customthe solvent removed in vacuo
  6. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-f491f5e6fe6047d08352473f4366aff1
Source dataset
uspto-grants-2002_10
Patent number
US06465497B2

Reaction notes

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