Dimethylformamide → 2-(Propan-2-yl)benzaldehyde

HRID 72625

Reaction equation

HRID 72625 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:10])[CH3:9].[Li]CCCC.CN([CH:19]=[O:20])C>C1COCC1.[Cl-].[NH4+]>[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:19]=[O:20])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 23475o-BromocumeneHCID 178418339Butyllithium

Product 1

HCID 5905362-(Propan-2-yl)benzaldehydeYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2-bromoisopropyl benzene (2.0 g, 10.0 mmole) in dry THF (20 mL), nBuLi (1.6 M in hexanes) (6.9 mL, 11.05 mmole) was added at −78° C. and the mixture was stirred at same temperature for one hour. DMF (0.9 g, 12.0 mmole) was added and the mixture was stirred at −78° C. for an additional half an hour, then allowed to stir at 0° C. for 15 min. The reaction mixture was diluted with saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine and dried over sodium sulfate. The solvent was evaporated to yield 2-isopropyl benzaldehyde (1.4 g).

Workup

  1. stirringthe mixture was stirred at −78° C. for an additional half an hour
  2. stirringto stir at 0° C. for 15 min
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-40ef821ef96e4e659befc53cd8ce9d1e
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Linked notes

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