Potassium Carbonate → Methyl 4-bromo-3-(2-methylallyloxy)benzoate

HRID 445920Notes

Reaction equation

HRID 445920 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([CH3:23])=[CH2:22]>CC(C)=O>[Br: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][CH2:22][C:21]([CH3:23])=[CH2:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propeneHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

HCID 57662790Methyl 4-bromo-3-(2-methylallyloxy)benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a heterogeneous mixture of methyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.49 mmol) and potassium carbonate (1.795 g, 12.98 mmol) in anhydrous acetone (50 mL) was added 3-bromo-2-methylprop-1-ene (2.62 mL, 26.0 mmol) at rt. The mixture was stirred rt for 4 h. The insoluble material was removed by filtration. The filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed sequentially with 1 N NaOH solution (30 mL), water (2×40 mL), and brine (30 mL). The organic solution was dried over anhydrous MgSO4 and concentrated under vacuum. The residue was applied to ISCO (80 g silica gel, 5-10% ethyl acetate/hexane) to provide the desired product, methyl 4-bromo-3-(2-methylallyloxy)benzoate (1.81 g, 6.35 mmol, 98% yield), as a colorless oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed sequentially with 1 N NaOH solution (30 mL), water (2×40 mL), and brine (30 mL)
  5. dry with materialThe organic solution was dried over anhydrous MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3b57585604344514b45d11fb0d3522a1
Source dataset
uspto-grants-2013_07
Patent number
US08476430B2

Reaction notes

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