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

HRID 1035665Notes

Reaction equation

HRID 1035665 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][CH3:24])=[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][CH3:24])=[O:22]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59443449HCID 59443449, compound

Product 1

HCID 249502262-Hydroxy-6-(3-hydroxyphenyl)-N-methyl-1-naphthamideYield 95%

Procedure

The compound is prepared by reaction of 2-methoxy-6-(3-methoxyphenyl)-N-methyl-1-naphthamide (250 mg, 0.78 mmol, 1 eq) with boron tribromide solution (3.89 mmol, 5 eq) according to method G. Purification by column chromatography with dichloromethane/methanol 98/2 as the eluent yielded the desired product in a yield of 95%, 217 mg.

Workup

  1. customPurification by column chromatography with dichloromethane/methanol 98/2 as the eluent

Sources & evidence

ORD record
ord-fe852f87302f4b50a886643f6531fc7c
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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