Diethyl Ether → HCID 13854299, compound

HRID 1200075Notes

Reaction equation

HRID 1200075 reaction equation
CN(C)P(N(C)C)N(C)C.Br[C:12](Br)([F:14])[F:13].[CH3:16][C:17]([CH3:37])([CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=1)[CH:18]=O.C(OCC)C>COCCOCCOCCOC>[CH3:16][C:17]([CH3:37])([CH:18]=[C:12]([F:14])[F:13])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6382DibromodifluoromethaneHCID 15355Hexamethylphosphorous triamideHCID 13849410HCID 13849410, compound

Product 1

HCID 13854299HCID 13854299, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 8189TriglymeSolvent2×

Conditions

Temperature
0 °C

Procedure

Hexamethylphosphorous triamide (0.65 g) was added portionwise to a stirred solution of dibromodifluoromethane (0.42 g) in triglyme (3 cm3) whilst being maintained at 0° C. under an atmosphere of nitrogen. After a period of 10 minutes a pale yellow colouration was observed and a solution of 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propan-1-al (0.3 g) in triglyme (2 cm3) was added. After stirring for a further two hours, whilst being maintained at 0° C., the reaction mixture was allowed to warm to the ambient temperature. When GLC examination of a worked-up portion of the reaction mixture showed an absence of further reaction, the reaction mixture was poured into diethylether and sequentially washed with water and brine. The solvent was removed by evaporation under reduced pressure to give a pale yellow liquid which was subjected to short-path distillation (boiling point 75° C./0.01 mm Hg). The residue was then subjected to column chromatography on silica gel using petroleum ether (boiling range 40°-60° C.) containing 5% by volume diethyl ether as eluent to give 2,2-dimethyl-1-(4-fluoro-3-phenoxybenzyloxy)-4,4-difluorobut-3-ene (0.045 g).

Workup

  1. temperaturewhilst being maintained at 0° C.
  2. temperatureto warm to the ambient temperature
  3. customan absence of further reaction
  4. washsequentially washed with water and brine
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customto give a pale yellow liquid which
  7. distillationwas subjected to short-path distillation (boiling point 75° C./0.01 mm Hg)
  8. additioncontaining 5% by volume diethyl ether as eluent

Sources & evidence

ORD record
ord-32e9c51893d949a186122f14043c66a3
Source dataset
uspto-grants-1990_02
Patent number
US04904677

Reaction notes

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