Sodium Carbonate → [4-(3-Methyl-2-pyridinyl)phenyl]methanol

HRID 1745006Notes

Reaction equation

HRID 1745006 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:7]1[C:2]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][OH:9])=[CH:12][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2208322-Bromo-3-methylpyridineHCID 27347064-(Hydroxymethyl)benzeneboronic acid

Product 1

HCID 21937278[4-(3-Methyl-2-pyridinyl)phenyl]methanolYield 47%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-3-methylpyridine (22.5 g, 0.1312 mol), 4-(hydroxymethyl)phenylboronic acid (25 g, 0.164 mol), Pd(PPh3)4 (9.5 g, 0.0082 mol), and sodium carbonate (200 g in 500 ml of water) in toluene (750 ml) were refluxed under nitrogen atmosphere for 15 h. Separated the toluene layer and distilled under reduced pressure to give a residue. The residue was then purified by column chromatography to yield [4-(3-methyl-2-pyridinyl)phenyl]methanol (12 g, 47%).

Workup

  1. temperaturewere refluxed under nitrogen atmosphere for 15 h
  2. customSeparated the toluene layer
  3. distillationdistilled under reduced pressure
  4. customto give a residue
  5. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-376ac21ba24e4dfcaab66bdbc6093b3a
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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