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Potassium Phosphate, Tribasic → Methyl 3-benzyloxy-5-phenylbenzoate

HRID 1096948
Notes
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Reaction equation

HRID 1096948 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:33]=[C:34](OS(C(F)(F)F)(=O)=O)[CH:35]=1)[C:29]([O:31][CH3:32])=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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.COCCOC>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([C:29]([O:31][CH3:32])=[O:30])[CH:33]=[C:34]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:35]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoate

Product 1

HCID 18945315Methyl 3-benzyloxy-5-phenylbenzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Phenylboronic acid (1.2 g), Pd(PPh3)4 (364 mg) and potassium phosphate (4 g) were added in that order to a DME (60 mL) solution of methyl 3-benzyloxy-5-{[(trifluoromethyl)sulfonyl]-oxy}benzoate (2.5 g), and stirred at 85° C. for 7 hours. The reaction liquid was filtered through Celite, concentrated under reduced pressure, and the residue was diluted with ethyl acetate, water was added to it, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a colorless oil.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate, water
  5. additionwas added to it
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-efe18fbcd3814819bf60a783ea75708d
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138197B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes