Sulfuric Acid → 1-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

HRID 2172964Notes

Reaction equation

HRID 2172964 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.CC(C[AlH]CC(C)C)C.C(OCC)(=[O:24])C.OS(O)(=O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH:11]=[O:24])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 71743245HCID 71743245, compound

Product 1

HCID 866727561-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(2-bromo-pyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.20 mmol) in toluene (30 mL) is added DIBAL-H (10.4 mL, 1M in toluene) at −78° C. The mixture is stirred 1 hour at −78° C. and warmed to room temperature. After 1 hour, ethyl acetate (30 mL) is added, followed by 1M aqueous solution of H2SO4 (30 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated to afford crude 1-(2-bromo-pyridin-4-yl)-cyclopropanecarbaldehyde (ES+ m/z 226.48; 228.47), which is used without purification.

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter 1 hour
  3. customPhases are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-60c577b3fe3249b7b888cd0f0e12bbba
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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