Water → [1,1'-Biphenyl]-4-amine, 3-nitro-

HRID 1479117Notes

Reaction equation

HRID 1479117 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>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>[N+:1]([C:4]1[CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 77705[1,1'-Biphenyl]-4-amine, 3-nitro-Yield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 2-nitro-4-bromoaniline (5 g, 23 mmol) in toluene was admixed with 2.8 g (23 mmol) of phenylboronic acid, 9.5 g (0.069 mol) of potassium carbonate and 1.3 g of tetrakis(triphenylphosphine)palladium. The mixture was heated to reflux for 4 hours and the reaction was stopped by adding 100 ml of water. The mixture was extracted with ethyl acetate and dried over sodium sulphate, and the solvent was removed under reduced pressure. Purification by column chromatography gave 3.6 g (73% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customPurification by column chromatography
  7. customgave 3.6 g (73% yield)

Sources & evidence

ORD record
ord-accbd3f9f0f1466ba57271101d51958b
Source dataset
uspto-grants-2016_08
Patent number
US09406848B2

Reaction notes

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