Sodium hydride → HCID 86644371, compound

HRID 219761

Reaction equation

HRID 219761 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[Cl:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([C:5]2[CH:4]=[C:3]([Cl:12])[C:2]([Cl:1])=[CH:7][C:6]=2[N+:8]([O-:10])=[O:9])[C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 104196Methyl 4-chlorophenylacetateHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzene

Product 1

HCID 86644371HCID 86644371, compoundYield 336.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 5 g of 1,2-dichloro-4-fluoro-5-nitrobenzene and 4.4 g of methyl 4-chlorophenylacetate in 70 ml of DMF is added, under a stream of nitrogen, to a suspension at −10° C. of 2.85 g of 60% NaH in 45 ml of DMF, and the temperature is maintained at −5° C. The mixture is reacted for 2 hours, while allowing the temperature to return to room temperature. The resulting mixture is poured onto ice, aqueous 10% NH4Cl solution is added and the mixture is extracted with ethyl acetate. The organic phase is dried, filtered and concentrated. 30 g of a brown oil are obtained, and are purified on a column with hexane and then with a 95/5 hexane/EtOAc mixture to give 3.18 g of oil.

Workup

  1. customThe mixture is reacted for 2 hours
  2. customto return to room temperature
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3e024f642e44fe9ba56d7c4d6cdcc3b
Source dataset
uspto-grants-2012_06
Patent number
US08202871B2

Linked notes

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