Iodine → 1-Cyclopropyl-2-(2-fluorophenyl)ethan-1-one

HRID 1945181Notes

Reaction equation

HRID 1945181 reaction equation
[Mg].II.[F:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Cl.CN(C)[C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16]>O1CCCC1.C(OCC)C>[F:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16]

Participants

7

Reactant 4

HCID 807IodineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 140273N,N-DimethylcyclopropanecarboxamideHCID 5462224Magnesium2×

Product 1

HCID 152899411-Cyclopropyl-2-(2-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 1000 ml round-bottomed flask is filled with magnesium (10.7 g, 0.44 mol). Iodine (0.2 g) is sublimated to the magnesium, then diethyl ether (240 ml) is added and under reflux, a solution of 2-fluorobenzyl chloride (47.8 ml, 0.4 mol) and diethyl ether (80 ml) is added to the reaction mixture. The mixture is refluxed for 2 hours and at this temperature a solution of cyclopropanecarboxylic acid dimethylamide (36.2 g, 0.32 mol), prepared according to example 1, and tetrahydrofuran (200 ml) are added. The reaction mixture is stirred for half an hour and under cooling aqueous hydrogen chloride (160 ml, 1:1) is added dropwise to the mixture. The organic layer is dried and the residue is fractionated in vacuo.

Workup

  1. temperatureunder reflux
  2. customprepared
  3. additionare added
  4. additionis added dropwise to the mixture
  5. customThe organic layer is dried

Sources & evidence

ORD record
ord-192ef729ef0f4e8eac16f35f9cdb9748
Source dataset
uspto-grants-2013_03
Patent number
US08394993B2

Reaction notes

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