1,2-Dimethoxyethane → HCID 21997568, compound

HRID 1977306Notes

Reaction equation

HRID 1977306 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][CH3:24])=[CH:17][CH:16]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:23]([O:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:16][CH:17]=1)[CH3:24]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 5981871-Bromo-4-(ethoxymethyl)benzeneHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 21997568HCID 21997568, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-methoxycarbonylphenylboronic acid (2.01 g) and 1-bromo-4-ethoxymethylbenzene (2.00 g) in a mixed solvent of ethylene glycol dimethyl ether (20 ml) and 2M aqueous sodium carbonate solution (6 ml) was added tetrakis(triphenylphosphine)palladium (0) (0.54 g). The mixture was heated at 80° C. for 5 hours. After cooling to room temperature, water (150 ml) was added to the reaction mixture and the resulting precipitate was collected by filtration, washed thoroughly with water and dried to give a crude solid. This solid was purified by column chromatography on silica gel (60 g) eluting successively with the following solvents: (1) n-hexane:ethyl acetate=50:1, (2) n-hexane:ethyl acetate=10:1. The fractions containing the object compound were concentrated and dried to give methyl 4-(4′-ethoxymethylphenyl)benzoate as a white solid (1.85 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed thoroughly with water
  4. customdried
  5. customto give a crude solid
  6. customThis solid was purified by column chromatography on silica gel (60 g)
  7. washeluting successively with the following solvents
  8. additionThe fractions containing the object compound
  9. concentrationwere concentrated
  10. customdried

Sources & evidence

ORD record
ord-29d9cffae83a461ca46fc3081f82cc5a
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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