2,4-Difluoroaniline → HCID 11312546, compound

HRID 896078Notes

Reaction equation

HRID 896078 reaction equation
FC1C=C(F)C=CC=1N.CC([O-])(C)C.[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:24])=[CH:19][CH:18]=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[OH:24])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 112086704-BROMO-2'-CHLOROBENZOPHENONEHCID 23676156Sodium t-butoxide

Product 1

HCID 11312546HCID 11312546, compoundYield 51.7%

Reagents, catalysts & solvents 2

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

Procedure

2,4-Difluoroaniline (0.28 ml; 2.7 mmol), NaOtBu (260 mg; 2.7 mmol), Pd(OAc)2 (10 mg; 0.04 mmol), R-(+)-BINAP (10 mg; 0.02 mmol) and (4-bromo-phenyl)-(2-chloro-phenyl)-methanone (200 mg; 0.67 mmol) are dissolved in dioxan (3 ml) and refluxed for 20 min. The reaction mixture is poured on water and extracted with TBME twice. The combined organic phases are dried over Na2SO4, evaporated to dryness and purified via chromatography (SiO2; TBME/hexanes 5/95>2/8) to yield the title compound (103 mg; 44%) as brownish crystals. Recrystallisation from acetone hexanes yields colorless crystals (48 mg; 21%).

Workup

  1. temperaturerefluxed for 20 min
  2. additionThe reaction mixture is poured on water
  3. extractionextracted with TBME twice
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated to dryness
  6. custompurified via chromatography (SiO2; TBME/hexanes 5/95>2/8)

Sources & evidence

ORD record
ord-b1e56401ea334921aa144689718b6042
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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