Iodine → HCID 19935801, compound

HRID 1931885Notes

Reaction equation

HRID 1931885 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[Mg].II.[CH2:13]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([N:20]1[CH2:24][CH2:23][C:22]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=2)([OH:25])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 698901-Benzyl-3-pyrrolidinoneHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 19935801HCID 19935801, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-3,5-difluorobenzene (10 g, 57.14 mmol) in dry tetrahydrofuran (60 mL), under nitrogen, was added magnesium turnings (1.37 g, 57.14 mmol) and one crystal of Iodine. The mixture started to reflux spontaneously and when all magnesium was consumed, a solution of 1-benzylpyrrolidin-3-one (10 g, 57.14 mmol) in dry tetrahydrofuran (40 mL) was added drop wise. The resulting mixture was heated to 60° C. for 2 h after which aqueous saturated ammonium chloride solution (50 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phase was dried (Na2SO4) and evaporated. Purification twice by flash chromatography on silica gel (isooctane/ethyl acetate, 1:1 and 6:4) gave the title compound (5.5 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 9), 198 (61), 133 (51), 132 (41), 91 (bp).

Workup

  1. temperatureto reflux spontaneously
  2. customwhen all magnesium was consumed
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  5. dry with materialthe combined organic phase was dried (Na2SO4)
  6. customevaporated
  7. customPurification twice by flash chromatography on silica gel (isooctane/ethyl acetate, 1:1 and 6:4)

Sources & evidence

ORD record
ord-408408a8fa07482abdcee1557e88739d
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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