Sodium Hydroxide → HCID 68577636, compound

HRID 1179122Notes

Reaction equation

HRID 1179122 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1B(O)O>OO>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2734659(2,4-Dichlorophenyl)boronic acid

Product 1

HCID 68577636HCID 68577636, compound

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the crude triflate obtained above (3 g), 2,4-dichloro-benzeneboronic acid (3.2 g, 1.1 eq), 1,1′-bis(diphenylphosphino-ferrocene)PdCl2 (315 mg, 0.025 eq) and K2CO3 (4.2 g, 2 eq), in toluene/acetone/water (26/26/6,5 mL) was heated at 80° C. for 3 h. The mixture was then treated with 1N NaOH (15 mL) and H2O2 30% (10 mL) for 20 min at r.t. to reduce the residual borane. The product was extracted with toluene, washed with brine and dried over anh. Na2SO4. The solids were filtered, the solvent was evaporated and the residue was purified by flash chromatography (silica gel, 100% cHex). The title compound was obtained as a clear oil (2.18 g, 9.58 mmol, 62%)

Workup

  1. extractionThe product was extracted with toluene
  2. washwashed with brine
  3. dry with materialdried over anh. Na2SO4
  4. filtrationThe solids were filtered
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography (silica gel, 100% cHex)

Sources & evidence

ORD record
ord-318e8d8530aa428aab51020e191435e8
Source dataset
uspto-grants-2007_10
Patent number
US07279474B2

Reaction notes

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