Dimethylformamide → HCID 107697243, compound

HRID 1054457Notes

Reaction equation

HRID 1054457 reaction equation
Br[C:2]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][O:7][CH2:6]1.C([Mg]Cl)(C)C.CN([CH:23]=[O:24])C>C1COCC1>[F:14][C:12]1[CH:11]=[CH:10][C:3]([O:4][CH:5]2[CH2:9][CH2:8][O:7][CH2:6]2)=[C:2]([CH:13]=1)[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 57582351HCID 57582351, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 107697243HCID 107697243, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-bromo-4-fluorophenoxy)tetrahydrofuran (50.0 g, 191 mmol) in 400 ml of dry THF at −78° C., isopropyl magnesium chloride (2M in THF) (240 ml, 479 mmol) was added drop wise, stirred the reaction mixture at room temperature for 4 h, again cooled the reaction mixture at −78° C., DMF (22.1 ml, 287 mmol) was added, stirred the reaction mixture at room temperature for 1 h, quenched with NH4Cl solution (400 ml), diluted with EtOAc (1.0 L), washed with water and brine solution, dried over sodium sulfate and concentrated to dryness to afford the title product 38.0 g (crude).

Workup

  1. temperatureagain cooled the reaction mixture at −78° C.
  2. stirringstirred the reaction mixture at room temperature for 1 h
  3. customquenched with NH4Cl solution (400 ml)
  4. additiondiluted with EtOAc (1.0 L)
  5. washwashed with water and brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c1f44e55c5374f36ab0fea882db50721
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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