Sulfuric Acid → HCID 18989454, compound

HRID 2395600Notes

Reaction equation

HRID 2395600 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21].[CH:22]([CH:24]=[CH2:25])=[O:23].OS(O)(=O)=O>CCCCCC.C1COCC1>[Br:13][C:14]1[C:15]([F:21])=[C:16]([CH:22]([CH:24]=[CH2:25])[OH:23])[C:17]([F:20])=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7847AcroleinHCID 7912DiisopropylamineHCID 676741-Bromo-2,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 18989454HCID 18989454, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

121.1 ml (0.194 mol) of a 1.6M solution of n-butyllithium in hexane are added dropwise to a solution, cooled to -10° C., of 21.5 g (0.212 mol) of diisopropylamine in 194 ml of anhydrous THF. The mixture is stirred for 10 min at -10° C. under a nitrogen atmosphere, is then cooled to -76° C. and a solution of 37.4 g (0.194 mol) of 1-bromo-2,4-difluorobenzene in 270 ml of anhydrous THF is added dropwise over 30 minutes, at a temperature below -70° C. The mixture is stirred for 2 minutes at -70° C. and then a solution of 14.7 g (0.212 mol) of acrolein in 30 ml of anhydrous THF is added dropwise over 10 minutes at a temperature below -60° C. The mixture is then stirred for 30 minutes at -70° C., and the temperature is then allowed to return to 0° C. The mixture is poured onto a mixture of 350 g of ice and 35 ml of concentrated H2SO4. Extraction with ether, washing with water, drying over Na2SO4, filtration, evaporation under vacuum and distillation are carried out. Weight obtained: 29 g (Yd.=60%) B.p.0.5 =86°-88° C.

Workup

  1. temperatureis then cooled to -76° C.
  2. stirringThe mixture is stirred for 2 minutes at -70° C.
  3. stirringThe mixture is then stirred for 30 minutes at -70° C.
  4. customto return to 0° C
  5. extractionExtraction with ether
  6. washwashing with water
  7. dry with materialdrying over Na2SO4, filtration, evaporation under vacuum and distillation
  8. customWeight obtained
  9. custom29 g (Yd.=60%) B.p.0.5 =86°-88° C.

Sources & evidence

ORD record
ord-c1227b3b41d94c048edd9354ad813baa
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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