Ethyl Bromide → 2-[[2-[4-(4-Trifluoromethylphenoxy)phenoxy]propionyl]]cyclopentane-1,3-dione

HRID 544189

Reaction equation

HRID 544189 reaction equation
C(Br)C.[Mg].[C:5]1(=[O:11])[CH2:9][CH2:8][C:7](=[O:10])[CH2:6]1.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:32]=[CH:31][C:17]([O:18][C:19]2[CH:30]=[CH:29][C:22]([O:23][CH:24]([CH3:28])[C:25](Cl)=[O:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1>O1CCCC1.CCOCC.O>[F:12][C:13]([F:33])([F:34])[C:14]1[CH:32]=[CH:31][C:17]([O:18][C:19]2[CH:30]=[CH:29][C:22]([O:23][CH:24]([CH3:28])[C:25]([CH:6]3[C:7](=[O:10])[CH2:8][CH2:9][C:5]3=[O:11])=[O:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6332Ethyl BromideHCID 774661,3-CyclopentanedioneHCID 5462224MagnesiumHCID 129060152-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Product 1

HCID 133091682-[[2-[4-(4-Trifluoromethylphenoxy)phenoxy]propionyl]]cyclopentane-1,3-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Ethyl bromide (6 g, 55 mmol) is added to magnesium turnings (1.34 g) in the presence of tetrahydrofuran (THF; 15 ml). After reaction is complete, the solution is diluted to 50 ml with THF cooled in an ice bath and cyclopentane-1,3-dione (50 mmol) is added rapidly with stirring. THF (250 ml) is added to this mixture and it is allowed to warm to RT. 2-[4-(4-Trifluoromethylphenoxy)phenoxy]propionic acid chloride (55 mmol) is added dropwise with stirring, and the mixture is allowed to stand at RT for 30 minutes. It is then poured into a mixture of ice, water and ether. The aqueous layer is extracted several times with ether. The combined ether extracts are washed with water, dried over sodium sulfate and the solvent is removed to give 2-[[2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl]]cyclopentane-1,3-dione (V; Y is H, Z is CF3, R1 is CH3 and n is one). ##STR5##

Workup

  1. customAfter reaction
  2. temperaturecooled in an ice bath
  3. stirringwith stirring
  4. extractionThe aqueous layer is extracted several times with ether
  5. washThe combined ether extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-1139decdbd2847ce89daa9fbccd70d57
Source dataset
uspto-grants-1984_05
Patent number
US04448965

Linked notes

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