(4-Propylphenyl)boronic acid → HCID 68783035, compound

HRID 1910357Notes

Reaction equation

HRID 1910357 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11](C)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)[CH2:16][CH3:17]>>[CH2:15]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:3]=2)=[CH:20][CH:19]=1)[CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 4100861(4-Propylphenyl)boronic acidHCID 57668727HCID 57668727, compound

Product 1

HCID 68783035HCID 68783035, compoundYield 128.5%

Procedure

2-(3-bromophenyl)-5-methylpyridine (20.0 g, 81.1 mmol) was reacted with 4-n-propylphenylboronic acid (15.9 g, 96.7 mmol) under standard Suzuki coupling condition. Kugelrohr distillation at 230° C. yielded 28.5 g of a viscous yellow liquid that was then purified by silica gel column chromatography with 15/85 ethyl acetate/hexane as the eluent, affording 14.0 g of pure material plus an additional impure fraction.

Workup

  1. distillationKugelrohr distillation at 230° C.

Sources & evidence

ORD record
ord-74af029f351f4460af7bc8e13372fe0c
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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