Potassium Phosphate, Tribasic → HCID 67396591, compound

HRID 714664Notes

Reaction equation

HRID 714664 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 67396591HCID 67396591, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Under argon, 500 mg (1.83 mmol) of dimethyl 5-bromoisophthalate together with 429 mg (2.75 mmol) of 2-chlorophenylboronic acid were dissolved in 8 ml of toluene, and 72 mg (0.18 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl, 84 mg (0.09 mmol) of tris(dibenzylideneacetone)dipalladium and 777 mg (3.66 mmol) of potassium phosphate were added successively. The mixture was heated to 110° C. and stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate. The solid was filtered off with suction and the residue was washed three times with in each case 10 ml of ethyl acetate. The combined filtrates were washed twice with in each case 10 ml of water. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically [Method 19]. This gave 305 mg (55% of theory) of the target compound.

Workup

  1. temperatureto cool to RT
  2. filtrationThe solid was filtered off with suction
  3. washthe residue was washed three times with in each case 10 ml of ethyl acetate
  4. washThe combined filtrates were washed twice with in each case 10 ml of water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-2ee51c66e615463fb8fb81460a9b6750
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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