Boron tribromide → 2-Hydroxy-6-(3-hydroxyphenyl)-N-phenyl-1-naphthamide

HRID 1035666Notes

Reaction equation

HRID 1035666 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]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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]([NH:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:22]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59443482HCID 59443482, compound

Product 1

HCID 249497082-Hydroxy-6-(3-hydroxyphenyl)-N-phenyl-1-naphthamideYield 23%

Procedure

The compound is prepared by reaction of 2-methoxy-6-(3-methoxyphenyl)-N-phenyl-1-naphthamide (217 mg, 0.57 mmol, 1 eq) with boron tribromide solution (3.39 mmol, 6 eq) according to method G. Purification by column chromatography with dichloromethane/methanol 95/5 as the eluent yielded the desired product in a yield of 23%, 47 mg.

Workup

  1. customPurification by column chromatography with dichloromethane/methanol 95/5 as the eluent

Sources & evidence

ORD record
ord-34449ea91f0a4fb582c22a119d07437c
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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