Potassium Phosphate, Tribasic → HCID 46314864, compound

HRID 645499Notes

Reaction equation

HRID 645499 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6](OS(C(F)(F)F)(=O)=O)[CH:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 230871615-Fluoro-2-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 46314864HCID 46314864, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoromethanesulfonic acid 5-fluoro-2-nitrophenyl ester (4.0 mmol) in DME (10 mL) are added phenylboronic acid (4.8 mmol), Pd(PPh3)4 (0.4 mmol), and K3PO4 (3.2 mmol) at room temperature. After stirring at 80° C. for 6 h, the reaction mixture is filtered through celite, and the filter cake is washed with AcOEt. The filtrate is diluted with water and extracted with ether (×2). The combined organic extracts are dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:AcOEt=6:1) to give the title compound; 1H NMR (CDCl3), δ 7.12-7.19 (2H, m), 7.29-7.32 (2H, m), 7.42-7.45 (3H, t), 7.94 (1H, dd).

Workup

  1. filtrationthe reaction mixture is filtered through celite
  2. washthe filter cake is washed with AcOEt
  3. additionThe filtrate is diluted with water
  4. extractionextracted with ether (×2)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (n-hexane:AcOEt=6:1)

Sources & evidence

ORD record
ord-e9418d8cd6fd4ade99ef55bac934df6a
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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