Trifluoroacetic acid → 2-Chloro-4-(2-hydroxy-phenylamino)-2'-methylbenzophenone

HRID 1264196Notes

Reaction equation

C([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])=[O:18])=[C:15]([Cl:28])[CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)C(F)(F)F>[Cl:28][C:15]1[CH:14]=[C:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[OH:5])[CH:27]=[CH:26][C:16]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])=[O:18]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 4-(2-tert-butoxy-phenylamino)-2-chloro-2′-methylbenzophenone (Compound 107) (1.33 g, 3.4 mmol) in a mixture of CH2Cl2 (5 ml) and trifluoroethanol (20 ml) was cooled to −5° C. under argron. Trifluoroacetic acid (423 mg, 3.7 mmol) was added dropwise and the reaction mixture was allowed to come to room temperature over 1 h. After 23 h at room temperature the reaction mixture was poured into saturated NaHCO3 and then extracted with EtOAc and CH2Cl2. The organic phases was collected, dried (MgSO4), filtered, and concentrated in vacuo to give the crude product. This was further purified by flash chromatography using EtOAc/pentane 1:4 as eluant.

Workup

extractionextracted with EtOAc and CH2Cl2
customThe organic phases was collected
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a40eb1594bdd4c15825370b83b5a0a83
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541670B2

Reaction notes

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