1,3-Dibromopropane → HCID 10589341, compound
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][CH3:23])=[O:21]>C(#N)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][CH3:23])=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
254.5 g of potassium carbonate and 654 cm3 of 1,3-dibromopropane are added to a solution of 153 g of methyl (2-hydroxyphenyl)acetate in 1400 cm3 of acetonitrile. The suspension obtained is refluxed for 20 hours, cooled to 20° C. and then filtered The filtrate is concentrated to dryness at 50° C. under reduced pressure. The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 8.8 cm, height 43 cm), eluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (95/5 by volume) and collecting fractions of 300 cm3. Fractions 18 to 53 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 130.6 g of methyl 2-(3-bromopropoxy)phenylacetate are obtained in the form of an orange-coloured oil.
Workup
- customThe suspension obtained
- temperatureis refluxed for 20 hours
- filtrationfiltered The filtrate
- concentrationis concentrated to dryness at 50° C. under reduced pressure
- customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 8.8 cm, height 43 cm)
- washeluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (95/5 by volume)
- customcollecting fractions of 300 cm3
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-39089bc71b1348aaa575bf8f47ddb07f
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451601
Reaction notes
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