Sodium Carbonate → HCID 57586574, compound

HRID 420395Notes

Reaction equation

HRID 420395 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6](Br)[CH:7]=1.[O:10]1[C:15]2[CH:16]=[CH:17][C:18](B(O)O)=[CH:19][C:14]=2[O:13][CH2:12][CH2:11]1.[C:23](=[O:26])([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.C(OCC)(=O)C.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:10]1[C:3]2[CH:2]=[CH:7][C:6]([C:15]3[CH:16]=[C:23]([OH:26])[CH:18]=[C:19]([C:18]4[CH:17]=[CH:16][C:15]5[O:10][CH2:11][CH2:12][O:13][C:14]=5[CH:19]=4)[CH:14]=3)=[CH:5][C:4]=2[O:9][CH2:12][CH2:11]1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 122803,5-DibromophenolHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acid

Product 1

HCID 57586574HCID 57586574, compoundYield 71.5%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3,5-dibromophenol (500 mg, 1.98 mmol) in dimethoxyethane (12.5 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, the solid tetrakis(triphenylphosphine)palladium(0) (496 mg, 0.43 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this period, a solution of 1,4-benzodioxane-6-boronic acid (536 mg, 2.98 mmol) in ethanol (12.5 mL) was added followed by a solution of sodium carbonate (421 mg, 3.97 mmol) in water (0.5 mL). The resulting light yellow suspension was stirred for 4 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (20 mL) and ethyl acetate (30 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo gave the colored residue which was purified by using an ISCO 120 column, eluting with 10-30% ethyl acetate in hexanes to afford 3,5-bis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenol (386 mg, 54%) as an amorphous light brown solid: ES(+)-HRMS m/e calculated for C22H18O5 (M+H)+ 363.1227, found 363.1226.

Workup

  1. waitAt this period
  2. stirringThe resulting light yellow suspension was stirred for 4 h
  3. temperatureat reflux
  4. temperatureThen, the reaction mixture was cooled to room temperature
  5. customThe two layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  7. washthe combined organic extracts were washed with water (100 mL) and brine solution (100 mL)
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo
  9. customgave the colored residue which
  10. customwas purified
  11. washeluting with 10-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-28cc10522fae4f19ac3f0ade72ffda54
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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