Potassium Phosphate, Tribasic → HCID 117992220, compound

HRID 531062Notes

Reaction equation

HRID 531062 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([O:21][CH:22]([CH3:24])[CH3:23])[C:19]=1I)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:17]=[C:18]([O:21][CH:22]([CH3:24])[CH3:23])[C:19]=1[C:37]1[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2856454-Fluorophenylboronic acidHCID 117992304HCID 117992304, compound

Product 1

HCID 117992220HCID 117992220, compoundYield 80.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium acetate (72 mg) was added to a mixture of ethyl 3-(benzyloxy)-4-iodo-5-isopropoxybenzoate (2.72 g), tripotassium phosphate (4.06 g), (4-fluorophenyl)boronic acid (1.78 g), tricyclohexylphosphine (20% toluene solution, 1.13 mL), toluene (20 mL), and water (10 mL), and the resultant mixture was stirred at 100° C. for 2 hours in an argon atmosphere. The reaction mixture was allowed to cool to room temperature, then diluted with ethyl acetate, and washed with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.03 g).

Workup

  1. washwashed with water and saturated saline in this order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f8b714a8b93d4e7d9bfece82b8fd0fe0
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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