Dichloromethane → 4'-Methyl-biphenyl-2-ylamine

HRID 2181876Notes

Reaction equation

HRID 2181876 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.ClCCl.[OH-].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 79799Tolylboronic acid

Product 1

HCID 15108204'-Methyl-biphenyl-2-ylamineYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-iodoaniline (5.0 g, 22.8 mmol), and 4-methylphenylboronic acid (3.1 g, 22.8 mmol) in tetrahydrofuran was treated under argon with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.37 g, 0.46 mmol), and a 5.0 N sodium hydroxide solution (9.1 mL, 45.7 mmol). The reaction mixture was heated under reflux for 24 hours, cooled to room temperature, and washed with a saturated, aqueous, sodium chloride solution. The aqueous phase was further extracted with ethyl acetate (3×). The combined organic phase was dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:12) to yield the title compound (3.26 g, 17.8 mmol, 78%) as an orange oil;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 hours
  3. washwashed with a saturated, aqueous, sodium chloride solution
  4. extractionThe aqueous phase was further extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica gel
  8. washeluting with a mixture of ethyl acetate-hexane (1:12)

Sources & evidence

ORD record
ord-604d2820708f4249ab8dfe1180326273
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…