Ammonium Chloride → 1-(4-Bromo-3-methylphenyl)ethanol

HRID 1501180Notes

Reaction equation

HRID 1501180 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[CH3:11][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 109215214-Bromo-3-methylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 790169431-(4-Bromo-3-methylphenyl)ethanolYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-3-methylbenzaldehyde (4 g, 20 mmol) in tetrahydrofuran (40 mL) was cooled to 0° C. then methylmagnesium bromide (20 mL, 1N in tetrahydrofuran) was dropped and the mixture was stirred at 0° C. to room temperature for 2 hours. Ammonium chloride aqueous (40 mL) was added and the mixture was extracted with dichloromethane (3*20 mL), dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give 1-(4-bromo-3-methylphenyl)ethanol as a colorless oil (4.0 g, 93%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3*20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-8c1fa9a18a484b72bc5b1a3ee187de28
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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