Boron tribromide → 2-(3-Hydroxyphenyl)quinolin-6-ol

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=1)[CH:7]=[CH:6]2.B(Br)(Br)Br>>[OH:19][C:15]1[CH:14]=[C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=3)[N:9]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 220646106-Methoxy-2-(3-methoxyphenyl)quinoline

Product 1

HCID 250694442-(3-Hydroxyphenyl)quinolin-6-olYield 10%

Procedure

The compound is prepared by reaction of 6-methoxy-2-(3-methoxyphenyl)quinoline (77 mg, 0.29 mmol, 1 eq) with boron tribromide (15 eq) according to method G. Purification by column chromatography with hexane/ethyl acetate 7/3 as the eluent yields the desired product in a yield of 10%, 7 mg.

Workup

customPurification by column chromatography with hexane/ethyl acetate 7/3 as the eluent

Sources & evidence

ORD record: ord-dcdb294dd069481abc4d45da19ed107c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546392B2

Reaction notes

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