Dimethylformamide → HCID 18406975, compound

HRID 842007Notes

Reaction equation

HRID 842007 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[CH3:10].[C:11](=O)=[O:12].CC(C)=O.C([Li])CCC.CN(C=O)C>C1COCC1>[Cl:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH:11]=[O:12])=[C:3]([CH3:10])[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 53247382-bromo-5-chloro-1,3-dimethylbenzeneHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 18406975HCID 18406975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-bromo-3,5-dimethyl chlorobenzene (6.5 g) in 50 mL anhydrous THF and cool to −78° C. (dry ice/acetone) under N2. Dropwise over 5 minutes add a solution of butyllithium (12.50 mL, 2.5M in hexanes) to the stirring solution of aryl bromide at −78° C. After 2 hours, dropwise add anhydrous DMF (5.0 mL) to the orange/red reaction solution and allow to warn to ambient temperature overnight while stirring under N2. Evaporate the yellow solution down to a yellow oil and partition between H2O (100 mL) and CH2Cl2 (100 mL). Extract the aqueous layer once with CH2Cl2, then pool the organic layers and dry over Na2SO4, filter and evaporate down to 5.0 g of yellow oil. Use without further purification. LCMS=169.6 (MH+)

Workup

  1. waitto warn to ambient temperature overnight
  2. customEvaporate the yellow solution down to a yellow oil
  3. custompartition between H2O (100 mL) and CH2Cl2 (100 mL)
  4. extractionExtract the aqueous layer once with CH2Cl2
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate down to 5.0 g of yellow oil
  8. customUse without further purification

Sources & evidence

ORD record
ord-0d1dcd9fa6c645cea252db478ec03282
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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