Water → HCID 15289940, compound

HRID 1975703Notes

Reaction equation

HRID 1975703 reaction equation
[Mg].[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.[CH:11]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12]1.O>C(OCC)C.O1CCCC1.CCCCCC.C1(C)C=CC=CC=1>[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:15]([CH:11]1[CH2:14][CH2:13][CH2:12]1)=[O:16]

Participants

9

Reactant 4

HCID 962WaterHCID 67968alpha-Bromo-o-fluorotolueneHCID 78705Cyclobutanecarbonyl chlorideHCID 5462224Magnesium

Product 1

HCID 15289940HCID 15289940, compoundYield 38.6%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

20 ml of anhydrous diethyl ether were added to 1.06 g (44 mmole) of metallic magnesium, and then a solution of 7.56 g (40 mmole) of 2-fluorobenzyl bromide in 10 ml of diethyl ether was slowly added dropwise to the resulting mixture, whilst stirring; the mixture was then stirred at room temperature for 1 hour. The resulting solution was slowly added dropwise to a solution of 4.74 g (40 mmole) of cyclobutanecarbonyl chloride in 30 ml of tetrahydrofuran, whilst cooling in a methanol-dry ice bath, over a period of 2 hours, and then the mixture was allowed to return to room temperature, whilst stirring, over a period of 2 hours. At the end of this time, 100 ml of water and 150 ml of diethyl ether were added to the reaction mixture, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, using a 9:1 by volume mixture of toluene and hexane as the eluent, to give 2.97 g of the title compound as a pale yellow oil.

Workup

  1. stirringthe mixture was then stirred at room temperature for 1 hour
  2. temperaturewhilst cooling in a methanol-dry ice bath, over a period of 2 hours
  3. customto return to room temperature
  4. stirringwhilst stirring, over a period of 2 hours
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-4450312ae001425581fd0a9940de3361
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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