Hydrochloric Acid → HCID 18786138, compound

HRID 1107861Notes

Reaction equation

HRID 1107861 reaction equation
CN([C:5](=[O:18])[CH:6]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17])[CH2:7][CH2:8][CH3:9])OC.O1CCC[CH2:20]1.C[Mg]Br.Cl>CCOCC>[Br:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH:6]([CH2:7][CH2:8][CH3:9])[C:5](=[O:18])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18786115HCID 18786115, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18786138HCID 18786138, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

6 g of N-methyl-O-methyl-2-(2-bromophenoxy)pentanohydroxamic acid and 190 ml of anhydrous tetrahydrofuran are placed in a 500 ml round-bottomed flask. The solution is cooled to -10° C. and 19 ml of a 3M solution of methylmagnesium bromide in ether are slowly added. The mixture is stirred for 45 minutes and 60 ml of a molar hydrochloric acid solution are slowly added. The mixture is extracted with 3×100 ml of ethyl ether. The combined organic phases are dried over magnesium sulphate, filtered and concentrated under vacuum to provide 5.13 g of 3-(2-bromophenoxy)-2-hexanone in the form of a colourless oil. Quantitative yield.

Workup

  1. extractionThe mixture is extracted with 3×100 ml of ethyl ether
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-09a42e3baeb0452f97fead1f8a6dcd67
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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