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

HRID 1423068Notes

Reaction equation

HRID 1423068 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.[H-].C([Al+]CC(C)C)C(C)C.CC[O:25]C(C)=O.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:25])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 71743245HCID 71743245, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a chilled (−78° C.) solution of 1-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at −78° C. for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2SO4 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated to afford crude 1-(2-bromopyridin-4-yl)-cyclopropanecarboxaldehyde which is used without purification. MS m/z 226.5, 228.5

Workup

  1. temperatureis then warmed to room temperature
  2. waitAfter 1 hour
  3. customThe organic phase is separated
  4. extractionthe aqueous layer is extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6b3987bf804e440ca28073feafebbac7
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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