Water → HCID 86642877, compound

HRID 624406Notes

Reaction equation

HRID 624406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O-:14])([O-])=O.[K+].[K+].[OH2:17]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:2]2=[C:3]([CH:11]=[O:14])[CH2:4][CH2:5][O:17][CH2:6][CH2:7]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

Product 1

HCID 86642877HCID 86642877, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chlorophenylboronic acid (6.10 g), EXAMPLE 314B (5.2 g), palladium(II) acetate (146 mg, 0.65 mmol), K2CO3 (13.5 g) and tetrabutylammonium bromide (10.5 g) was added water (200 mL). The mixture was stirred at 50° C. for 4 hours. The mixture was diluted with ethyl acetate (400 mL) and washed with water (3×) and brine and dried over Na2SO4. After filtration and concentration, the residue was loaded on a column and eluted with 5 to 20% ethyl acetate in hexane to give the pure product.

Workup

  1. washwashed with water (3×) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration
  4. washeluted with 5 to 20% ethyl acetate in hexane
  5. customto give the pure product

Sources & evidence

ORD record
ord-08c04df0becc444eaed24001c3ccbda4
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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