Potassium Acetate → HCID 89582740, compound

HRID 2276808Notes

Reaction equation

HRID 2276808 reaction equation
I[C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=2)=[CH:4][CH:3]=1.[BH:21]([OH:23])[OH:22].O[C:25]([C:28](O)([CH3:30])[CH3:29])([CH3:27])[CH3:26].OC(C(O)(C)C)(C)C.CC([O-])=O.[K+]>O1CCOCC1.O>[CH3:26][C:25]1([CH3:27])[C:28]([CH3:30])([CH3:29])[O:23][B:21]([C:2]2[CH:20]=[CH:19][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=3)=[CH:4][CH:3]=2)[O:22]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 43327322HCID 43327322, compoundHCID 178459132HCID 178459132, compound

Product 1

HCID 89582740HCID 89582740, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(4-Iodophenoxy)-2-trifluoromethyl benzonitrile (20 g, 51.4 mmol) was treated with bis-pinacol boronate (13 g, 51.4 mmol, NetChem), KOAc (10 g, 102.8 mmol), and PdCl2dppf*CH2Cl2 (2.1 g, 2.57 mmol) in 50 mL dioxane at 100° C. for 20 hours. The reaction mixture was diluted with 500 mL water and extracted with 2×300 mL EtOAc. The combined organic layers were washed with 250 mL brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica using a gradient of EtOAc (20% max) in hexane as the eluent to give 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-(trifluoromethyl)benzonitrile (11.45 g, 57%). 1H NMR (400 MHz, CDCl3): 7.93-7.86 (2 H, m), 7.79-7.71 (1 H, m), 7.36-7.32 (1 H, m), 7.17-7.12 (1 H, m), 7.10-7.04 (2 H, m), 1.38-1.34 (12 H, s).

Workup

  1. extractionextracted with 2×300 mL EtOAc
  2. washThe combined organic layers were washed with 250 mL brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica using a gradient of EtOAc (20% max) in hexane as the eluent

Sources & evidence

ORD record
ord-e7434c198db24438a038a6164eafdb6e
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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