Hydrochloric Acid → 4-Chloro-3-ethylbenzaldehyde

HRID 19778Notes

Reaction equation

HRID 19778 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[Li]CCCC.CN([CH:19]=[O:20])C.Cl>C(OCC)C.CCCCCC.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH:19]=[O:20])=[CH:3][C:4]=1[CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 441194014-Bromo-1-chloro-2-ethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 552650954-Chloro-3-ethylbenzaldehydeYield 62.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.319 g of 4-bromo-1-chloro-2-ethyl-benzene (20 mmol) in 50 ml diethylether, cooled to 0° C., were added dropwise 12.3 ml of 1.6M n-BuLi in hexane. After 30 min. stirring at 0° C. and 2 h at RT, a solution of 2.43 ml DMF (31 mmol) in 10 ml diethylether was added dropwise (temperature raised from 20 to 28° C.). After 1 h additional stirring at RT, the reaction mixture was acidified with 2N HCl, diluted with 150 ml water and extracted with diethylether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by flash column chromatography (heptane/AcOEt: 95/5) to yield 2.1 g of a colorless oil. MS (ISP) 168.1 (M+H)+.

Workup

  1. temperature(temperature raised from 20 to 28° C.)
  2. stirringAfter 1 h additional stirring at RT
  3. extractionextracted with diethylether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (heptane/AcOEt: 95/5)

Sources & evidence

ORD record
ord-71d96795f3b74acda950d9f94cb7eed1
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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