Water → 4-(4-Chlorophenyl)-N-methylaniline

HRID 405136Notes

Reaction equation

HRID 405136 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 2757052Benzenamine, 4-bromo-N-methyl-

Product 1

HCID 156227444-(4-Chlorophenyl)-N-methylaniline

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-N-methylaniline (0.7 mL, 5.4 mmol), (4-chlorophenyl)boronic acid (967 mg, 6.2 mmol), Pd(dppf)Cl2 (440 mg, 0.5 mmol), and K2CO3 (1.5 g, 10.8 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-c91907fe4f2e4e5e90f3fa3bea5698b6
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

Loading…