Diethyl Ether → 1-(2-Bromo-3-chloro phenyl)butan-1-ol

HRID 1927308Notes

Reaction equation

HRID 1927308 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].C(OCC)C.[Br:11][C:12]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].[Cl-].[NH4+]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[Br:11][C:12]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]([OH:15])[CH2:1][CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 234639272-Bromo-3-chlorobenzaldehydeHCID 178455855HCID 178455855, compound

Product 1

HCID 585727921-(2-Bromo-3-chloro phenyl)butan-1-olYield 62%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, zinc chloride (0.68 g, 4.97 mmol) was added to a 2.0 M solution of n-propyl magnesium chloride in diethyl ether (12.42 mL, 24.93 mmol), and the mixture was stirred at room temperature. After stirring for 0.5 hours, a solution of 2-bromo-3-chlorobenzaldehyde (4.36 g, 19.87 mmol), which had been obtained in Reference example 5(5b), in tetrahydrofuran (10 mL) was added dropwise thereto. After stirring for 2 hours under ice cooling, a saturated aqueous ammonium chloride solution (20 mL) was added thereto. The mixture obtained was extracted with ethyl acetate (20 mL×2). After that, the organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=5/1) to give the title compound as a white solid (3.23 g, yield 62%).

Workup

  1. stirringAfter stirring for 0.5 hours
  2. additionwas added dropwise
  3. stirringAfter stirring for 2 hours under ice cooling
  4. customThe mixture obtained
  5. extractionwas extracted with ethyl acetate (20 mL×2)
  6. washAfter that, the organic layers were washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-264ffd6ae3e64b41afe54be4725e45df
Source dataset
uspto-grants-2012_05
Patent number
US08183272B2

Reaction notes

Loading…