Acetone → HCID 10586821, compound

HRID 1684922Notes

Reaction equation

HRID 1684922 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[CH3:18][C:19]([CH3:21])=[O:20].Cl>O1CCCC1>[Br:9][C:10]1[C:11]([F:17])=[C:12]([C:19]([OH:20])([CH3:21])[CH3:18])[C:13]([F:16])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 676741-Bromo-2,4-difluorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 10586821HCID 10586821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

6.3 ml of a 2M solution of lithium diisopropylamide in tetrahydrofuran (standardized beforehand at 0.86M) are introduced under a stream of argon into 5 ml of tetrahydrofuran in a round-bottomed flask. The mixture is cooled to −78° C. and 0.59 ml of 1-bromo-2,4-difluorobenzene is added dropwise thereto. The mixture is stirred at −78° C. for 30 min and acetone is added via four fractions of 0.5 ml. The reaction medium is run into 20 ml of 1N hydrochloric acid after returning to ambient temperature. The organic phase, extracted with diethyl ether, is subsequently washed twice with 20 ml of water, separated, dried over magnesium sulphate and concentrated under reduced pressure. The oil obtained is purified by chromatography on silica gel, elution being carried out with a heptane/ethyl acetate mixture. 0.50 g of compound is obtained.

Workup

  1. customafter returning to ambient temperature
  2. extractionThe organic phase, extracted with diethyl ether
  3. washis subsequently washed twice with 20 ml of water
  4. customseparated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe oil obtained
  8. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-a34aaf5c98a1401b899b8deb58472b3a
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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