Ammonium Chloride → Methyl 3-nitro-5-phenylbenzoate

HRID 1070404Notes

Reaction equation

HRID 1070404 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+].[CH3:18][O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23](I)[CH:22]=1.[Cl-].[NH4+]>O1CCOCC1.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>[CH3:18][O:19][C:20]([C:21]1[CH:22]=[C:23]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)=[O:31]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 7020599Methyl 3-iodo-5-nitrobenzoate

Product 1

HCID 69687208Methyl 3-nitro-5-phenylbenzoateYield 73.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Phenylboronic acid (2.14 g, 17.59 mmol), potassium phosphate (4.50 g, 21.20 mmol), tetrakis(triphenylphosphine)palladium(0) (0.283 g, 0.24 mmol) and 3-iodo-5-nitro-benzoic acid methyl ester (3.00 g, 9.77 mmol) in dioxane (30 mL) were heated at 80° C. for 3 h. Saturated ammonium chloride was added and the product was extracted, washed with water, brine, dried over magnesium sulfate, and concentrated to dryness. Purification by chromatography gave 1.85 g of 5-nitro-biphenyl-3-carboxylic acid methyl ester, as a white solid.

Workup

  1. extractionthe product was extracted
  2. washwashed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-75a58f7a5a744f7d81693cf57fe99d4c
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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