Ammonium Chloride → 2-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanol

HRID 1027688Notes

Reaction equation

HRID 1027688 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([Mg]Cl)[CH:15]=[CH:16][CH:17]=1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[C:7]([CH2:8][CH:9]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:11])[CH:17]=2)[OH:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 581389672-(2-Bromopyridin-3-yl)acetaldehydeHCID 178478982HCID 178478982, compound

Product 1

HCID 581389372-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanolYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(2-bromopyridin-3-yl)acetaldehyde (864 mg, 4.7 mmol) in THF (10 mL) at 0° C. was added (3-chlorophenyl)magnesium chloride (0.5M in THF, 14 mL, 7.04 mmol). The mixture was stirred at room temperature for 4 hours then treated with ammonium chloride (sat) at 0° C., extracted with ethyl acetate. The combined ethyl acetate layer was washed with brine, dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel gave 2-(2-bromopyridin-3-yl)-1-(3-chlorophenyl)ethanol (490 mg, 35% yield) as white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-299e5ae468af476598fcc9ee1a040681
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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