1,3-Dibromopropane → HCID 10935561, compound

HRID 384782Notes

Reaction equation

HRID 384782 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 10935561HCID 10935561, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82.5 °C

Procedure

In a 100 mL volume glass flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser were placed 10.2 g (54.9 mmol) of methyl 4-hydroxy-3-methoxybenzoate (purity: 98 wt. %), 12.5 g (60.4 mmol) of 1,3-dibromopropane (purity: 99 wt. %), 8.5 g (60.4 mmol) of potassium carbonate (purity: 98 wt. %), and 30 mL of acetonitrile. The resulting mixture was refluxed under stirring at 80-85° C. in an argon gas atmosphere for 8 hours. After the reaction was complete, the reaction mixture was filtered and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (gel: Wako gel C-200, eluent: n-hexane), to give 15.1 g (isolated yield: 88.8%, purity: 98% in terms of area percentage by high performance liquid chromatography) of methyl 4-(3-bromopropoxy)-3-methoxybenzoate as a white crystalline product.

Workup

  1. customIn a 100 mL volume glass flask equipped with a stirrer
  2. temperatureThe resulting mixture was refluxed
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography (gel: Wako gel C-200, eluent: n-hexane)

Sources & evidence

ORD record
ord-425e12705cbe467ea797b7c3233c0735
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

Loading…