Cesium carbonate → 4-Nitro[1,1'-biphenyl]-3-amine

HRID 878468Notes

Reaction equation

HRID 878468 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[N+:9]([C:4]1[CH:3]=[CH:2][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:5]=1[NH2:6])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 125954834-Nitro[1,1'-biphenyl]-3-amineYield 96.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-bromo-2-nitroaniline (217 mg, 1.0 mmol), phenylboronic acid (122 mg, 1.0 mmol), tetrakis-(triphenylphosphine)palladium (55 mg, 0.05 mmol) and cesium carbonate (650 mg, 2.0 mmol) was added 3 mL of ethyleneglycol dimethyl ether (DME). The reaction was heated to 80° C. and stirred under nitrogen atmosphere overnight. The mixture was filtered through a celite pad. The filtrate was concentrated and purified by biotage column chromatography to give 4-nitrobiphenyl-3-amine (207 mg)

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. concentrationThe filtrate was concentrated
  3. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-9dda66ac93304f8f8fa78ac1d950b963
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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