Boron tribromide → (2-Hydroxy-6-(3-hydroxyphenyl)naphthalene-1-yl)(piperazin-1-yl)methanone

HRID 1035668Notes

Reaction equation

HRID 1035668 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

Reactant 2

HCID 25134Boron tribromideHCID 59443464HCID 59443464, compound

Product 1

HCID 24949710(2-Hydroxy-6-(3-hydroxyphenyl)naphthalene-1-yl)(piperazin-1-yl)methanoneYield 60%

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

  1. customPurification by column chromatography
  2. extractionExtraction of the aqueous phase with ethyl acetate

Sources & evidence

ORD record
ord-2846101758d5443d81b6656c1b9436ac
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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