3-Bromoquinoline → 3-(4-Methoxyphenyl)quinoline

HRID 1035597Notes

Reaction equation

HRID 1035597 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](OB(O)O)=[CH:16][CH:15]=1>>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 214133-BromoquinolineHCID 147699944-Methoxyphenyl boric acid

Product 1

HCID 41342973-(4-Methoxyphenyl)quinolineYield 89%

Procedure

The compound is prepared by the reaction of 3-bromoquinoline (500 mg, 2.40 mmol, 1 eq) with 4-methoxyphenylboric acid (365 mg, 2.40 mmol, 1 eq) according to method A in 18 h. Purification by column chromatography with a mixture of hexane/ethyl acetate 9/1 yielded the desired product as a white solid in a yield of 89% (504 mg).

Workup

  1. customPurification by column chromatography
  2. additionwith a mixture of hexane/ethyl acetate 9/1

Sources & evidence

ORD record
ord-3af15a95a39245f1b3406c4d578b0cf8
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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