Water → HCID 22387982, compound

HRID 1072881Notes

Reaction equation

HRID 1072881 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:8]3[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:9]=3[O:10][C:11]=2[CH3:12])=[C:4]([Cl:23])[CH:3]=1.[C:24]1(OB(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(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.C1(C)C=CC=CC=1>[Cl:23][C:4]1[CH:3]=[C:2]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][C:5]=1[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:9]=2[O:10][C:11]=1[CH3:12]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 22387902HCID 22387902, compound

Product 1

HCID 22387982HCID 22387982, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To unpurified 3-(4-bromo-2-chlorobenzyl)-5-(methoxycarbonyl)-2-methylbenzo[b]furan (4.00 g) were added a solution of phenylboric acid (1.34 g) in ethanol (3 ml), tetrakis(triphenylphosphine)palladium (0.40 g), sodium carbonate (1.59 g), water (7.50 g) and toluene (30 ml) and the mixture was heated under reflux for 80 min. After cooling, the insoluble matter was removed by filtration through Celite and the filtrate was washed with ethyl acetate and water. Saturated brine was added to the filtrate. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give an oil (3.50 g) containing the object compound as main component. The oil was used in the next step without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 80 min
  3. temperatureAfter cooling
  4. customthe insoluble matter was removed by filtration through Celite
  5. washthe filtrate was washed with ethyl acetate and water
  6. additionSaturated brine was added to the filtrate
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8d6dae92583247de9cb5f501a303ee10
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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