1-Bromo-4-iodobenzene → HCID 86720791, compound

HRID 1776080Notes

Reaction equation

HRID 1776080 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.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]>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:18])[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 20511057N-(2-Methylphenyl)naphthalen-1-amine2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 86720791HCID 86720791, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-(o-tolyl)naphthalen-1-amine (Compound 20) (2.0 g, 8.6 mmol), 1-bromo-4-iodobenzene (8.67 g, 30 mmol), Pd(dppf)Cl2 (0.365 g, 0.5 mmol), potassium tert-butoxide (1.96 g, 20 mmol) in toluene was degassed and heated at 110° C. overnight. The resulting mixture was worked up with ethyl acetae/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1. After removal of solvents, a yellow solid (Compound 21) was obtained, 0.45 g in 13.5% yield.

Workup

  1. customwas degassed
  2. dry with materialdried over Na2SO4
  3. custompurified by flash column
  4. customAfter removal of solvents

Sources & evidence

ORD record
ord-834b40d693824f8d8aafc53a01196fda
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

Loading…