Ammonium Chloride → 2-(Benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol

HRID 595767Notes

Reaction equation

HRID 595767 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5](I)=[CH:4][CH:3]=1.[CH2:10]([O:17][CH2:18][CH:19]=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH4+].[Cl-]>C1COCC1>[CH2:10]([O:17][CH2:18][CH:19]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)[OH:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 108989(Phenylmethoxy)acetaldehydeHCID 467367846-Bromo-2-chloro-3-iodopyridine

Product 1

HCID 903324402-(Benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanolYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to −78° C., followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at −78° C. for 1 h. 2-(benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0° C. and stirred for 2 h. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54 g, yield: 95%). MS (M+H)+: 344.

Workup

  1. additionfollowed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol)
  2. temperaturethe resulting mixture warmed to 0° C.
  3. stirringstirred for 2 h
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53c90e3617d948519066383c203178fe
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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