1,2-Dibromoethane → HCID 43532237, compound

HRID 1908079Notes

Reaction equation

HRID 1908079 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].C([O-])([O-])=O.[K+].[K+].[Br:20][CH2:21][CH2:22]Br>CC(C)=O>[Br:20][CH2:21][CH2:22][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 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 43532237HCID 43532237, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 4-hydroxy-3-methoxy-benzoate (2.0 g, 11 mmol) in acetone (330 mL) was added K2CO3 (6.1 g, 44 mmol) followed by 1,2-dibromoethane (6.2 g, 2.8 mL, 33 mmol). The mixture was stirred for 2 d at 75° C. The mixture was cooled to ambient temperature and the solids were removed by filtration. The filtrate was concentrated and the residue was purified by column chromatography (10-25% ethyl acetate/hexanes) to give methyl 4-(2-bromoethoxy)-3-methoxybenzoate. ESI-MS m/z calc. 288.0. found 289.1 (M+1)+; Retention time: 1.47 minutes (3 min run).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solids were removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography (10-25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-63d29a46ce5b4957af85176166caf601
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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