2-Bromo-1,4-difluorobenzene → HCID 89618599, compound

HRID 1476750Notes

Reaction equation

HRID 1476750 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14].O=[C:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C1COCC1>[F:14][C:8]1[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=1[C:16]1[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH2:19][CH:20]=1

Participants

5

Reactant 3

HCID 678622-Bromo-1,4-difluorobenzeneHCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 89618599HCID 89618599, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.0 M Isopropyl magnesium chloride solution in THF (163 mL, 324.3 mmol) was added to a solution of 2-bromo-1,4-difluorobenzene (62.5 g, 324.3 mmol) in THF (350 mL) at −40° C. and stirring was continued at 5° C. for 1 h. tert-Butyl 2-oxopyrrolidine-1-carboxylate (Step-1) (73 g, 392 mmol) in THF (150 mL) was added dropwise to above reaction mixture at −40° C. and stirring was continued at 10° C. for 2 h. Reaction mixture was quenched with saturated NH4Cl solution, extracted with EtOAc, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 76 g of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued at 10° C. for 2 h
  3. customReaction mixture
  4. customwas quenched with saturated NH4Cl solution
  5. extractionextracted with EtOAc
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3217d26f18624a8fb770ca68ae0c2486
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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