Dimethylformamide → HCID 18677628, compound

HRID 2269259Notes

Reaction equation

HRID 2269259 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]2[O:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[F:16][C:17]([F:25])([F:24])[C:18]([F:23])([F:22])C([O-])=O.[Na+].CN(C=O)C>[Cu]I.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]([F:23])([F:22])[C:17]([F:25])([F:24])[F:16])=[CH:3][C:4]=1[CH:10]1[O:15][CH2:14][CH2:13][CH2:12][O:11]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2733305Sodium pentafluoropropionateHCID 143787592-(5-Bromo-2-methoxyphenyl)-1,3-dioxane

Product 1

HCID 18677628HCID 18677628, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
140 °C

Procedure

A 50 ml round bottom flask equipped with Dean-Stark trap and reflux condenser was charged with Compound 38 (1.0 g, 3.66 mmol), sodium pentafluoropropionate (1.29 g, 6.95 mmol) and copper(I) iodide (1.46 g, 7.69 mmol), DMF (15 ml)-toluene (6 ml). The slurry was heated to 120-140° C. (bath temperature) and toluene (6 ml) was removed by distillation. The reaction mixture was heated at 140° C. (inner temperature) for 15 h. The mixture was diluted with water (40 ml)-toluene (15 ml)-ethyl acetate (60 ml). The mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate. The filtrate was washed with water, and brine, dried(MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(10:1-5:1) to give Compound 39 (1.07 g) as a pale yellow oil

Workup

  1. customA 50 ml round bottom flask equipped with Dean-Stark trap
  2. temperaturereflux condenser
  3. customwas removed by distillation
  4. additionThe mixture was diluted with water (40 ml)-toluene (15 ml)-ethyl acetate (60 ml)
  5. filtrationThe mixture was filtered through a pad of celite
  6. washthe filter cake was washed with ethyl acetate
  7. washThe filtrate was washed with water, and brine, dried(MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give crude product
  10. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(10:1-5:1)

Sources & evidence

ORD record
ord-c38e9ce7280a4441aec7740c52c0189f
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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