Toluene → Biphenyl, 3,5-diisopropyl-4-amino-

HRID 2041830Notes

Reaction equation

HRID 2041830 reaction equation
Br[C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].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.O>[CH:12]([C:4]1[CH:3]=[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]=1[NH2:6])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 117801144-Bromo-2,6-diisopropylaniline

Product 1

HCID 3025997Biphenyl, 3,5-diisopropyl-4-amino-Yield 57%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

4-bromo-2,6-diisopropylaniline (16 g, 62.5 mmol), (PPh3)4Pd (2.2 g, 1.9 mmol), phenylboronic acid (11 g, 87.5 mmol), K3PO4 (26 g, 187 mmol), 400 mL of toluene and 40 mL of water were charged and heated up to reflux for overnight. The reaction mixture was purified by column and distillation method to give 9 g liquid (57% yield).

Workup

  1. temperatureheated up
  2. temperatureto reflux for overnight
  3. distillationThe reaction mixture was purified by column and distillation method

Sources & evidence

ORD record
ord-1ed70af69d13430eaafb7c9b3d16fade
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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