Potassium Phosphate, Tribasic → HCID 68278912, compound

HRID 508186Notes

Reaction equation

HRID 508186 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1(C)[C:32](C)(C)OB(C(C)=C)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([C:28]([CH3:32])=[CH2:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 10739136HCID 10739136, compoundHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 68278912HCID 68278912, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 4-(benzyloxy)-2-(trifluoromethylsulfonyloxy)benzoate (i-1c) (6.8 g, 17.4 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (2.9 g, 17.4 mmol), Pd(OAc)2 (195 mg, 0.87 mmol), S-Phos (71 mg, 0.174 mmol) and K3PO4 (11 g, 52 mmol) were mixed in THF (70 ml). The mixture was stirred at 75° C. for 24 h. The mixture was diluted with H2O, and extracted with EtOAc. The combined organics were dried and concentrated. The residue was purified by flash chromatography (PE/EA=10:1) to afford the title compound. LCMS (ESI) calc'd for C18H18O3 [M+H]+: 391. found: 391.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organics were dried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (PE/EA=10:1)

Sources & evidence

ORD record
ord-87b630a1297a4008b395f5283a6f8a72
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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