1,3-Dibromopropane → HCID 18414623, compound

HRID 843625Notes

Reaction equation

HRID 843625 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-c46b5cb7ec524c3fb9727af81deac5d8
Source dataset
uspto-grants-2002_04
Patent number
US06380191B1

Reaction notes

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