Triethylsilane → 2-Bromo-4-ethyl-1-fluorobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 84A (9.8 g, 45 mmol) in trifluoroacetic acid (20 mL) was added triethylsilane (14.3 mL, 90 mmol). After stirring at 50° C. for 6 h, the reaction was quenched with 100 mL of saturated NaHCO3 solution and extracted with diethyl ether (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The resulting residue was distilled at 200° C. to give 84B (85% purity).
Workup
- customthe reaction was quenched with 100 mL of saturated NaHCO3 solution
- extractionextracted with diethyl ether (3×)
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- distillationThe resulting residue was distilled at 200° C.
Sources & evidence
- ORD record
- ord-df1c88522eeb4b98929b7a61f8f0ba01
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622585B2
Reaction notes
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