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

HRID 1599164Notes

Reaction equation

HRID 1599164 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C(#N)C.C(OCC)(=O)C>[Br:7][CH2:8][CH2:9][CH2:10][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 15525522HCID 15525522, compound

Product 1

HCID 22417251Benzyl [2-(3-bromopropoxy)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.2 g of potassium carbonate and 40 cm3 of 1,3-dibromopropane are added to a solution of 4.84 g of benzyl [(2-hydroxy)phenyl]acetate in 100 cm3 of acetonitrile. The mixture is stirred at the reflux temperature for 20 hours and then cooled to room temperature before being filtered. The filtrate is concentrated to dryness under reduced pressure and the residue obtained is taken up in 200 cm3 of ethyl acetate. The solution is washed with twice 100 cm3 of water then with 150 cm3 of brine, and is dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (particle size 0.06-0.200 height 30 cm, diameter 5 cm), eluting with a mixture of cyclohexane and ethyl acetate (95:5 by volume) and collecting fractions of 100 cm3. Fractions 18 to 28 are concentrated to dryness under reduced pressure (2.7 kPa). 2.0 g of benzyl [2-(3-bromopropoxy)phenyl]acetate are obtained in the form of an oil.

Workup

  1. filtrationbefore being filtered
  2. concentrationThe filtrate is concentrated to dryness under reduced pressure
  3. customthe residue obtained
  4. washThe solution is washed with twice 100 cm3 of water
  5. dry with materialwith 150 cm3 of brine, and is dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure (2.7 kPa)
  7. customThe oil obtained
  8. customis chromatographed on a silica gel column (particle size 0.06-0.200 height 30 cm, diameter 5 cm)
  9. washeluting with a mixture of cyclohexane and ethyl acetate (95:5 by volume)
  10. customcollecting fractions of 100 cm3
  11. concentrationFractions 18 to 28 are concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-41308f5529cf469c845ab13e654876e3
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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