Benzyl Bromide → 2-(Benzyloxy)-6-chloropyridine

HRID 1518963Notes

Reaction equation

HRID 1518963 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:16][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:9])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 112644642-(Benzyloxy)-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Add benzyl bromide (1 mL, 8.38 mmol) to a solution of 6-chloropyridin-2-ol (2 g, 15.4 mmol), potassium carbonate (3.41 g, 24.7 mmol) in DMF (20 mL) heat to 80° C. and stir for two hours. Quench reaction mixture with water, then extract three times with 20 mL EtOAc. Combine the organic washings and wash with water (20 mL); dry over sodium sulphate; filter; collect the filtrate; and concentrate under vacuum. Purify via normal phase silica gel flash column chromatography using a gradient of 0-50% ethyl acetate in petroleum ether to give the title compound as a clear oil. MS: (m/z): 220 (M+1).

Workup

  1. customQuench
  2. customreaction mixture with water
  3. extractionextract three times with 20 mL EtOAc
  4. washwash with water (20 mL)
  5. dry with materialdry over sodium sulphate
  6. filtrationfilter
  7. customcollect the filtrate
  8. concentrationand concentrate under vacuum
  9. customPurify via normal phase silica gel flash column chromatography

Sources & evidence

ORD record
ord-179ef6769d4241af81fb50d075c35f41
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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