Dimethylformamide → HCID 86042697, compound

HRID 1698395Notes

Reaction equation

HRID 1698395 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[Li]CCCC.CN([CH:25]=[O:26])C.[Cl-].[NH4+]>C1COCC1>[C:13]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:25]=[O:26])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 666719634-Bromo-2-(1,1-dimethylethyl)-N,N-diethylbenzenamineHCID 178418339Butyllithium

Product 1

HCID 86042697HCID 86042697, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3.6 g (13 mmol) of (4-bromo-2-tert-butylphenyl)-diethylamine are diluted in 100 ml of THF, under a stream of nitrogen. The medium is cooled to −78° C. and then 7.8 ml (20 mmol) of a 2.5M solution of nBuLi are added. After stirring for 45 minutes, 1.5 ml (20 mmol) of DMF are added and the solution is brought back to ambient temperature. After 15 minutes, the mixture is poured into a saturated solution of ammonium chloride and then extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate and then concentrated to dryness. 3.1 g of 3-tert-butyl-4-diethylaminobenzaldehyde are obtained in the form of a yellow oil (yield=100%).

Workup

  1. customis brought back to ambient temperature
  2. waitAfter 15 minutes
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fb66f79ea88d45e2a2f2498efbdd22a7
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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