Dichloromethane → 2-Amino-4'-chlorobiphenyl

HRID 2181879Notes

Reaction equation

HRID 2181879 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.ClCCl.[OH-].[Na+]>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]>[Cl: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

6

Reactant 4

HCID 6344DichloromethaneHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 742994-Chlorophenylboronic acid

Product 1

HCID 2622612-Amino-4'-chlorobiphenylYield 79%

Reagents, catalysts & solvents 1

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

Procedure

The title compound was prepared from 2-iodoaniline (5.0 g, 22.83 mmol), 4-chlorophenylboronic acid (3.57 g, 22.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.373 g, 0.46 mmol), and a 5.0 M sodium hydroxide solution (9.1 mL, 45.65 mmol) according to the procedure and in the same manner as described in Example 60, step a. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:12) to yield 4′-chloro-1,1′-biphenyl-2-amine (3.67 g, 18.0 mmol, 79%) as an orange oil;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:12)

Sources & evidence

ORD record
ord-c8c5d7e30d6b44fbb3d20ecc92368660
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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