Boron tribromide → 3-Hydroxy-5-(6-hydroxynaphthalene-2-yl)-N-phenylbenzamide

HRID 1035656Notes

Reaction equation

HRID 1035656 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28]C)[CH:24]=3)[CH:19]=2)[CH:17]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].B(Br)(Br)Br>>[OH:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([OH:28])[CH:24]=3)[CH:19]=2)[CH:17]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59443453HCID 59443453, compound

Product 1

HCID 249500413-Hydroxy-5-(6-hydroxynaphthalene-2-yl)-N-phenylbenzamideYield 11%

Procedure

The compound is prepared by reaction of 3-methoxy-5-(6-methoxynaphthalene-2-yl)-N-phenylbenzamide (300 mg, 0.78 mmol, 1 eq) with boron tribromide solution (5 eq) according to method G. Purification by column chromatography with hexane/dichloromethane 1/99 yielded the desired product in a yield of 11%, 32 mg.

Workup

  1. customPurification by column chromatography with hexane/dichloromethane 1/99

Sources & evidence

ORD record
ord-1d6300d13bc14f81907aedddce946f36
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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