Sodium Methoxide → HCID 81429573, compound

HRID 1487869Notes

Reaction equation

HRID 1487869 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[I:13].[CH3:14][O-:15].[Na+]>CO>[I:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH2:2][O:15][CH3:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57446309Methyl 4-(bromomethyl)-3-iodobenzoate2×

Product 1

HCID 81429573HCID 81429573, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250-mL round-bottom flask, was placed a mixture of methyl 4-(bromomethyl)-3-iodobenzoate (compound 20.1, 3.0 g, 8.5 mmol) and sodium methoxide (1.8 g, 33 mmol) in methanol (100 mL). The resulting solution was stirred for 2 h at 50° C., then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL) and the solids were filtered off. The filtrate was concentrated under reduced pressure to yield 2.0 g (77%) of the title compound as a yellow solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (50 mL)
  5. filtrationthe solids were filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aaaf2cc5db924fa1a5f800055870307d
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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