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

HRID 1945182Notes

Reaction equation

HRID 1945182 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.COC(C)(C)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 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent2×

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 tert-butyl methyl ether (240 ml) is added and under boiling, a solution of 2-fluorobenzyl chloride (47.8 ml, 0.4 mol) and tert-butyl methyl 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. customprepared
  2. additionare added
  3. additionis added dropwise to the mixture
  4. customThe organic layer is dried

Sources & evidence

ORD record
ord-33c31a54c06c4508bd40ead91c820eee
Source dataset
uspto-grants-2013_03
Patent number
US08394993B2

Reaction notes

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