Potassium Phosphate, Tribasic → HCID 70819337, compound

HRID 1525750Notes

Reaction equation

HRID 1525750 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][C:3]=1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[C:21]2[CH:26]=[C:25](I)[C:24]([O:28][CH3:29])=[CH:23][C:22]=2[CH3:30])[CH:14]=[CH:13][CH:12]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][O:28][C:24]1[C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][C:21]([C:19]2[C:20]3[C:15](=[CH:14][CH:13]=[CH:12][C:11]=3[C:3]3[CH:4]=[C:5]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:6]([O:8][CH3:9])=[CH:7][C:2]=3[CH3:1])[CH:16]=[CH:17][CH:18]=2)=[C:22]([CH3:30])[CH:23]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 70854788HCID 70854788, compound

Product 1

HCID 70819337HCID 70819337, compoundYield 175%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5a (0.20 g, 0.32 mmol), phenylboronic acid (0.12 g, 0.96 mmol), Pd(PPh3)4 (0.055 g, 0.048 mmol) and K3PO4, (0.31 g, 1.44 mmol) in 5 mL of toluene was stirred at 110° C. for 18 hours. The resulting mixture was allowed to come to room temperature, quenched with water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2Cl2:hexanes 1:2) afforded 0.14 g (0.28 mmol, 87%) of 6 as a white solid.

Workup

  1. customto come to room temperature
  2. customquenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (CH2Cl2:hexanes 1:2)

Sources & evidence

ORD record
ord-7cc696f7c3ff47fbbba2bbbb89a23f63
Source dataset
uspto-grants-2015_07
Patent number
US09085511B2

Reaction notes

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