2-Bromopyridine → HCID 54273101, compound

HRID 744125Notes

Reaction equation

HRID 744125 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:19][CH:20]=1>N1C=CC=CC=1.[Cu]=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 54273101HCID 54273101, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromopyridine (1.1 ml, 11.5 mmol) and potassium carbonate (2.76 g, 20.0 mmol) were added to a solution of methyl 3-hydroxyphenylacetate (1.66 g, 9.99 mmol) in anhydrous pyridine (12 ml). The vigorously stirred reaction mixture was heated to 90° C. under a nitrogen atmosphere and then copper (II) oxide (1.99 g, 25.0 mmol) was added under a positive nitrogen flush. The reaction mixture was heated under reflux for 16 hours, allowed to cool and diluted with dichloromethane. The mixture was filtered through hyflo and concentrated in vacuo. The residue was purified by flash chromatography on silica eluting with 1:3 ethyl acetate/petrol (60°-80° ) then 1:2 ethyl acetate/petrol (60°-80° ) to give methyl [3-(2-pyridyloxy)phenyl]acetate as a pale straw-coloured oil (1.85 g, 78%); δH (360 MHz, CDCl3) 3.63 (2H, s, CH2), 3.69 (3H, s, COOCH3), 6.90 (1H, d, J 8 Hz, ArH), 6.99(1H, m, ArH), 7.06 (2H, m, ArH), 7.11 (1H, d, J 8 Hz, ArH), 7.34 (1H, t, J 8 Hz, 5'-H), 7.67 (1H, m, ArH), 8.19 (1H, m, 6"-H), m/z 243 (M+).

Workup

  1. customThe vigorously stirred reaction mixture
  2. customflush
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 16 hours
  5. temperatureto cool
  6. additiondiluted with dichloromethane
  7. filtrationThe mixture was filtered through hyflo
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica eluting with 1:3 ethyl acetate/petrol (60°-80° )

Sources & evidence

ORD record
ord-b9498b169205415098942984b4076d19
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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