Ethyl Bromide → 1-(3-Fluorophenyl)propan-1-ol
Reaction equation
[CH2:1](Br)[CH3:2].[Mg].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]>C1COCC1>[F:5][C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:1][CH3:2])[CH:11]=[CH:12][CH:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
18 L ethyl bromide were dissolved in 30 L of THF and added dropwise to a suspension of 6 kg of magnesium in 30 L of THF. The reaction solution was next stirred for two hours at 65° to 75° C. and then cooled to 0 to 10° C. 15 kg of 3-fluorobenzaldehyde in 60 L of THF were added while cooling with ice over a period of 6 hr and the reaction solution was stirred overnight at room temp. The reaction solution was quenched with saturated ammonium chloride solution at 0°-10° C. The reaction solution was stirred for one hour, organic layer separated and concentrated. The concentrate was extracted with 40 L of DCM and washed with 30 L of 5% HCl solution. The solvent was removed in vacuo. After drying, 20 kg of 1-(3-Fluoro -phenyl)-propan-1-ol were obtained as a brown oil and taken as such to the next step.
Workup
- temperaturewhile cooling with ice over a period of 6 hr
- stirringthe reaction solution was stirred overnight at room temp
- customThe reaction solution was quenched with saturated ammonium chloride solution at 0°-10° C
- stirringThe reaction solution was stirred for one hour
- customorganic layer separated
- concentrationconcentrated
- extractionThe concentrate was extracted with 40 L of DCM
- washwashed with 30 L of 5% HCl solution
- customThe solvent was removed in vacuo
- customAfter drying
Sources & evidence
- ORD record
- ord-34780d2d851d46e1807c9ffdb822e700
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608740B2
Reaction notes
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