Boron tribromide → HCID 24950042, compound

HRID 1035657Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5](/[CH:21]=[CH:22]/[C:23]([NH:25][CH3:26])=[O:24])[CH:6]=[C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=3)[CH:10]=2)[CH:8]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:4]=[C:5](/[CH:21]=[CH:22]/[C:23]([NH:25][CH3:26])=[O:24])[CH:6]=[C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[CH:10]=2)[CH:8]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 59443466HCID 59443466, compound

Product 1

HCID 24950042HCID 24950042, compoundYield 13%

Procedure

The compound is prepared by reaction of (E)-3-[3-methoxy-5-(6-methoxy-naphthalene-2-yl)phenyl]-N-methylacrylamide (200 mg, 0.58 mmol, 1 eq) with boron tribromide solution (5 eq) according to method G. Purification by preparative thin-layer chromatography with dichloromethane/methanol 90/10 yielded the desired product in a yield of 13%, 25 mg.

Workup

customPurification by preparative thin-layer chromatography with dichloromethane/methanol 90/10

Sources & evidence

ORD record: ord-73d34ec59d3c45469f2d91aada158978
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546392B2

Reaction notes

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