Water → HCID 86642503, compound

HRID 1520620Notes

Reaction equation

HRID 1520620 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[CH2:7][CH2:6][CH:5]([OH:17])[CH2:4][C:3]=2[CH:11]=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

Product 1

HCID 86642503HCID 86642503, 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 (6.88 g), EXAMPLE 224A (4.65 g), palladium(II) acetate (131 mg), K2CO3 (18.24 g) and tetrabutylammonium bromide (14.18 g) was added water (200 mL). The mixture was stirred at 50° C. for 4 hours, cooled, and 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 5-20% ethyl acetate in hexane to give the title compound.

Workup

  1. temperaturecooled
  2. washwashed with water (3×) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. washeluted with 5-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-96f4d7345fb94299adc69528f5c34d8c
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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