2,4-Difluoroaniline → HCID 22349585, compound

HRID 896080Notes

Reaction equation

HRID 896080 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].FC1C=C(F)C=CC=1N>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[OH:9])[CH:7]=1

Participants

7

Reactant 4

HCID 97092,4-DifluoroanilineHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 22349583HCID 22349583, compound

Product 1

HCID 22349585HCID 22349585, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
135 °C

Procedure

(5-Bromo-2-methoxy-phenyl)-(4-bromo-phenyl)-methanone (16.5 g; 44.6 mmol), R-(+)-BINAP (1.38 g; 2.23 mmol), Pd(OAc)2 (1.499 g; 6.69 mmol), PPh3 (3.03 g; 11.6 mmol), Cs2CO3 (29.1 g; 89.2 mmol) and 2,4-Difluoroaniline (6.8 ml; 66.9 mmol) are dissolved in dioxane (600 ml) and heated to 135° C. for 1.5 hours. The reaction mixture is cooled, filtered, evaporated and purified via chromatography (SiO2; acetone/hexanes 5:95>10:90) to yield the title product as yellow crystals (10.7 g; 57%).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customevaporated
  4. custompurified via chromatography (SiO2; acetone/hexanes 5:95>10:90)

Sources & evidence

ORD record
ord-e6e99841617c474f9cc97f60c155bb2e
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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