Ethanol → 6-Methyl-biphenyl-3-ylamine

HRID 2216030Notes

Reaction equation

HRID 2216030 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[CH3:8][C:7]1[C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][C:4]([NH2:9])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 122478006-Methyl-biphenyl-3-ylamineYield 47.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a dried flask was added 3-bromo-4-methyl-phenylamine (1 g, 5.37 mmol), phenyl boronic acid (2.62 g, 21.5 mmol), aqueous Na2CO3 (2M, 21.5 mL, 43 mmol), ethanol (21.5 mL), and toluene (43 mL). The flask was sparged with Ar, and Pd(PPh3)4 (1.55 g, 1.34 mmol) was added. The reaction mixture was stirred and heated at 80° for 18 hrs, then cooled to room temperature. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with water and brine, then dried over MgSO4. The solvent was removed in vacuo and the residue was purified via column chromatography (SiO2, 5% DCM/hexane) to afford a yellow oil (463 mg, 47%). This was directly used in the next step.

Workup

  1. additionwas added
  2. temperatureheated at 80° for 18 hrs
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified via column chromatography (SiO2, 5% DCM/hexane)

Sources & evidence

ORD record
ord-fa08c0cb10ba4c6c818c18fb37271f36
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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