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

HRID 1035598Notes

Reaction equation

HRID 1035598 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:15]=[C:16](OB(O)O)[CH:17]=[CH:18][CH:19]=1>>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([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:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 214133-BromoquinolineHCID 221738233-Methoxyphenylboric acid

Product 1

HCID 41342983-(3-Methoxyphenyl)quinolineYield 70%

Procedure

The compound is prepared by the reaction of 3-bromoquinoline (200 mg, 0.96 mmol, 1.06 eq) and 3-methoxyphenylboric acid (138 mg, 0.91 mmol, 1 eq) according to method A in 19 h. Purification by column chromatography with a mixture of hexane/ethyl acetate 3/1 yields the desired product in a yield of 70% (147 mg).

Workup

  1. customPurification by column chromatography
  2. additionwith a mixture of hexane/ethyl acetate 3/1

Sources & evidence

ORD record
ord-16ec92c871ce4ff7b4ef9e211713f5a4
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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