2,4-Difluoroaniline → HCID 45280639, compound

HRID 473468Notes

Reaction equation

HRID 473468 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:18]=1.[F:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1[NH2:22].P.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:18]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67359866HCID 67359866, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 45280639HCID 45280639, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

For the synthesis of the title compound, 0.52 g (0.0020) mol of 8-chloro-1-hydroxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.26 g (0.0020 mol) of 2,4-difluoroaniline, 2 spatula tips of Pd(OAc)2, 0.14 g of phosphine ligand and 0.90 g (0.0094 mol) of NaOtert-Bu in 10 ml of toluene and 2 ml of tert-BuOH are reacted by method O. Purification is carried out by column chromatography (flash; silica gel, 90% hexane+10% ethyl acetate). C21H15F2NO2 (Mr=351.36); GC 35.3 min

Sources & evidence

ORD record
ord-42b8162b32ce46d987df08b08c3f9fc5
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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