Diethyl Ether → HCID 53934353, compound

HRID 1156523Notes

Reaction equation

HRID 1156523 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([CH:9](Br)[CH:10](Br)[C:11]#[N:12])=[CH:5][CH:4]=1.C[O-].[Na+].C[CH2:21][O:22]CC>CO>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:22][CH3:21])=[CH:10][C:11]#[N:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 20534840HCID 20534840, compound

Product 1

HCID 53934353HCID 53934353, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

3-(4-(Trifluoromethyl)phenyl)-2,3-dibromopropionitrile (2098 grams) was dissolved in methanol and chilled to 5° C. in an ice-bath. Next, over a 2 hour period, sodium methylate (95%) was added keeping the temperature between 5°-10° C. Following this the reaction mixture was allowed to warm to room temperature, was stirred for 33 hours, and was then stripped to near dryness. Upon the addition of 8 l. ether the mixture was slurried, slowly filtered, and stripped again, resulting in a brown oil. NMR analysis confirmed that the oil was the desired mixture of product.

Workup

  1. custombetween 5°-10° C
  2. temperatureto warm to room temperature
  3. additionUpon the addition of 8 l
  4. filtrationslowly filtered
  5. customresulting in a brown oil
  6. additionmixture of product

Sources & evidence

ORD record
ord-a8da91a1861c4f74b7fb58f8d722e8f5
Source dataset
uspto-grants-1982_06
Patent number
US04336264

Reaction notes

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