Sodium Carbonate → HCID 68193313, compound

HRID 1626796Notes

Reaction equation

HRID 1626796 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[OH:10][CH2:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.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>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:16]2[CH:17]=[C:12]([CH2:11][OH:10])[CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 685274-Bromobenzyl bromideHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 1

HCID 68193313HCID 68193313, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

4-Bromobenzyl bromide (6.1 g, 22 mmol) and [3-(hydroxymethyl)phenyl]boronic acid (3.0 g, 20 mmol) were dissolved in a mixed solvent of toluene (40 mL), ethanol (30 mL) and water (20 mL), and tetrakis(triphenylphosphine)palladium (1.1 g, 1.0 mmol) and sodium carbonate (4.2 g, 40 mmol) were added under a nitrogen atmosphere, followed by heating to reflux for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.75 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (4.7 g, 17 mmol) as a yellow oil (yield 85%).

Workup

  1. additionwere added under a nitrogen atmosphere
  2. temperatureby heating
  3. temperatureto reflux for 6 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialsubsequently the organic layer was dried over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  8. concentrationa fraction corresponding to the Rf value=0.75 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bddce5c5bbf6485c800eff12239b01a9
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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