Hydrochloric Acid → HCID 66839351, compound

HRID 546655Notes

Reaction equation

HRID 546655 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.Br[CH2:18][CH2:19][CH2:20][Cl:21].Cl>C1COCC1.CCCCCC.C(OCC)(=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 676173-Fluorophenylacetic acidHCID 178418339Butyllithium

Product 1

HCID 66839351HCID 66839351, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-fluorophenylacetic acid (500 mg) in THF (15 mL) was stirred at −78° C. for 5 minutes. A 2.66 M solution of n-butyl lithium in hexane (2.44 mL) was added, and the reaction solution was stirred at −78° C. for three hours. Thereafter, the reaction solution was stirred at 0° C. for one hour, 1-bromo-3-chloropropane was added, and the reaction solution was stirred at room temperature for 17 hours. Thereafter, ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 734 mg of the title compound. The property values of the compound are as follows.

Workup

  1. stirringThereafter, the reaction solution was stirred at 0° C. for one hour
  2. stirringthe reaction solution was stirred at room temperature for 17 hours
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b138057cee144250a3a97cd09feaea65
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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