Diethyl Ether → HCID 131715333, compound

HRID 255919Notes

Reaction equation

HRID 255919 reaction equation
[F:1][CH:2]=[C:3](CBr)[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[OH:26].[H-].[Na+].[CH3:29]COCC>CN(C)C=O.[Cl-].[Na+].O>[F:1]/[C:2](/[CH2:29][O:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[Cl:18])=[CH:3]\[CH2:4][N:5]1[C:6](=[O:15])[C:7]2=[CH:14][CH:13]=[CH:12][CH:11]=[C:8]2[C:9]1=[O:10]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 84492,4-DichlorophenolHCID 24758Sodium hydrideHCID 54187565HCID 54187565, compound

Product 1

HCID 131715333HCID 131715333, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Solid 1-fluoro-2-bromomethyl-3-phthalimidopropene (0.60 g) is added to a previously prepared mixture of 2,4-dichlorophenol (0.33 g) and sodium hydride dispersion (96 mg of 55-60% oil dispersion) in dimethylformamide (10 ml) at room temperature. Stirring is continued for 3 hours, then brine is added and the product is isolated by ether extraction. The extracted material is essentially pure (Z)-1-fluoro-(2',4'-dichlorophenoxy)methyl -3-phthalimidopropene (0.67 g; 88% yield). A small portion is recrystallized from hexane/dichloromethane whereupon the analytical sample is obtained as colorless plates; mp. 115°-116° C.

Sources & evidence

ORD record
ord-c404dacebf344b2ead2cf9297c5fd7d7
Source dataset
uspto-grants-1987_10
Patent number
US04699928

Reaction notes

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