Hydrochloric Acid → 2-(4-Bromophenyl)-1,1,1-trifluoropropan-2-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:14][Mg]Br.Cl>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])([CH3:14])[C:9]([F:11])([F:12])[F:10])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Commercial 1-(4-bromophenyl)-2,2,2-trifluoroethanone (1 g, 4 mmoles) in diethyl ether (8 mL) was cooled to −78° C. for the addition of commercial methylmagnesium bromide (2.65 mL, 7.9 mmoles, 3 M in diethyl ether). The cloudy reaction media was allowed to reach room temperature and stirred overnight. The reaction mixture was transferred to a separatory funnel containing 1.2 M hydrochloric acid (20 mL). This aqueous layer was extracted 3 times with ethyl acetate (30 mL). The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The clear oil was pure enough to be used without further purification.
Workup
- customThe cloudy reaction media
- customto reach room temperature
- customThe reaction mixture was transferred to a separatory funnel
- extractionThis aqueous layer was extracted 3 times with ethyl acetate (30 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customto be used without further purification
Sources & evidence
- ORD record
- ord-4abc8ecae4874cec9af756b8ee61da4a
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07407959B2
Reaction notes
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