Ammonium Chloride → 1-(4-Bromo-3-chlorophenyl)ethanol
Reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13].[Cl-].[NH4+]>O1CCCC1>[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:1])=[CH:7][C:6]=1[Cl:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of methylmagnesium bromide (4.8 mL, 3M, 14.4 mmol) was added dropwise to the solution of 4-bromo-3-chlorobenzaldehyde (1.52 g, 7.0 mmol) in tetrahydrofuran at −40° C. Then the mixture was stirred at 25° C. for 3 hrs. Saturated ammonium chloride solution (10 mL) was added to the mixture. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1) to give 1-(4-bromo-3-chlorophenyl)ethanol as a white solid (1.32 g, 81%). 1H NMR (300 MHz, d6-DMSO): 7.69 (d, J=8.1, 1H), δ 7.53 (d, J=0.9, 1H), 7.19 (dd, J1=8.1, 1H J2=0.9, 1H), 5.38 (d, J=3.6, 1H), δ 4.70 (m, 1H), 1.30 (d, J=6.6, 3H).
Workup
- concentrationThe mixture was concentrated
- customto give a residue
- customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-fb1657f355904ce680ec073d72dd52ff
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206128B2
Reaction notes
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