Cyclohexanecarbonyl chloride → Cyclohexyl 2-Fluorobenzyl Ketone
Reaction equation
[Cl-].[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Zn+].[CH:11]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:17]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 36 ml of 2-fluorobenzylzinc chloride (0.5 M sol. in tetrahydrofuran) and 0.008 g of dichlorobis(triphenylphosphine)palladium(II) stirred at 0° C. was added dropwise via a syringe 2.14 ml of cyclohexanecarbonyl chloride. Afterwards, the reaction mixture was stirred at r.t. for 4 h, quenched with an aqueous saturated solution of ammonium chloride (25 ml), extracted with 20 ml of EtOAc, which was dried (Na2SO4) and evaporated to dryness in vacuo affording 3.52 g of the title compound as a crude, which could be used in the following step without further purification.
Workup
- stirringAfterwards, the reaction mixture was stirred at r.t. for 4 h
- customquenched with an aqueous saturated solution of ammonium chloride (25 ml)
- extractionextracted with 20 ml of EtOAc, which
- dry with materialwas dried (Na2SO4)
- customevaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-ee37b3bbe8884342a72654bff4d2cc0e
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071197B2
Reaction notes
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