Ammonium Chloride → HCID 67403681, compound

HRID 1931856Notes

Reaction equation

HRID 1931856 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[Mg].[C:11]([N:18]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Cl-].[NH4+]>O1CCCC1>[F:9][C:4]1[CH:3]=[C:2]([C:20]2([OH:23])[CH2:21][CH2:22][N:18]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:19]2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 67403681HCID 67403681, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-3,5-difluorobenzene (3.13 g, 16.2 mmol) in dry tetrahydro-furan (40 mL), under nitrogen, was added magnesium turnings (0.39 g, 16.2 mmol). The mixture was refluxed for 1 h, cooled to ambient temperature and a solution of 1-N-boc-3-pyrrolidinone (2.0 g, 10.8 mmol) in dry tetrahydrofuran (10 mL) was added drop wise. The resulting mixture was refluxed 1 h, cooled to ambient temperature, aqueous saturated ammonium chloride solution (40 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic phase was dried (MgSO4), filtered and evaporated to give the title compound (3.38 g). MS m/z (rel. intensity, 70 eV) 299 (M+, 1), 243 (42), 198 (49), 168 (31), 127 (28), 57 (bp).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureThe resulting mixture was refluxed 1 h
  3. temperaturecooled to ambient temperature
  4. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a23b96d904f0497cbbb676c63c93034b
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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