2-Bromopyridine → 2-(Pyridin-2-yl)phenol

HRID 1268655Notes

Reaction equation

HRID 1268655 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])O1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+].C(COC)OC>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.O>[OH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 1354892212-(Pyridin-2-yl)phenolYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

9.5 g (˜43 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 6.8 g (˜43 mmol) of 2-bromopyridine, 1.5 g (1.3 mmol) of Pd(PPh3)4, and 16 g (116 mmol) of K2CO3 were added to a 250 mL round bottle flask, along with a solvent mixture of 120 mL of dimethoxyethane and 150 mL of water. The mixture was heated to reflux for 24 hours under nitrogen. The reaction mixture was extracted with ethyl acetate and the organic phase was separated on silica gel column with 15% ethyl acetate as elute solvent. ˜5.9 g (yield ˜80%) of 2-(2-hydroxyphenyl)pyridine was obtained as a colorless liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours under nitrogen
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. customthe organic phase was separated on silica gel column with 15% ethyl acetate
  5. washas elute solvent

Sources & evidence

ORD record
ord-9f370215fbb14d9c989c0b8702e8aa45
Source dataset
uspto-grants-2007_04
Patent number
US07198859B2

Reaction notes

Loading…