2,4-Difluoroaniline → HCID 60167138, compound

HRID 473505Notes

Reaction equation

HRID 473505 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][O:20]C(=O)C)=[CH:16][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1.[F:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH2:28].P>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH:28][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][OH:20])=[CH:16][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1

Participants

7

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24404PhosphineHCID 67498510HCID 67498510, compound

Product 1

HCID 60167138HCID 60167138, compoundYield 20%

Reagents, catalysts & solvents 3

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

Procedure

In accordance with general method O, 0.67 g (0.19 mmol) of acetic acid 2-(8-chloro-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yloxy)-ethyl ester, 0.26 g (0.0020 mol) of 2,4-difluoroaniline, 0.04 g of Pd(OAc)2, 0.14 g of phosphine ligand and 0.70 g (7.3 mmol) of Na—O-tert-butylate are reacted in 10 ml of toluene and 2 ml of tert-BuOH. Yield: 20%; m.p.: 138° C.

Sources & evidence

ORD record
ord-f2fa35a963284b5a895ce659ace0eaca
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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