Boron tribromide → (2-Hydroxy-6-(3-hydroxyphenyl)naphthalene-1-yl)(piperazin-1-yl)methanone
Reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]1)=[O:22].B(Br)(Br)Br>>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22]Participants
3
Procedure
The compound is prepared by reaction of tert-butyl 4-(2-methoxy-6-(3-methoxyphenyl)-1-naphthoyl)piperazine-1-carboxylate (200 mg, 0.42 mmol, 1 eq) with boron tribromide solution (2.5 ml, 2.52 mmol, 6 eq) according to method G. Purification by column chromatography was not necessary. Extraction of the aqueous phase with ethyl acetate yields the desired product in a yield of 60%, 88 mg.
Workup
- customPurification by column chromatography
- extractionExtraction of the aqueous phase with ethyl acetate