Butanal → HCID 67980648, compound

HRID 1427489Notes

Reaction equation

HRID 1427489 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].[CH:11](=[O:15])[CH2:12][CH2:13][CH3:14].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([CH:11]([OH:15])[CH2:12][CH2:13][CH3:14])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 261ButanalHCID 25517Ammonium ChlorideHCID 450407122-Bromo-5-iodobenzonitrile

Product 1

HCID 67980648HCID 67980648, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-8 °C

Procedure

A round bottom flask was charged with the 2-bromo-5-iodobenzonitrile (2.00 g, 6.49 mmol) and THF (9 mL). Solution cooled down to −8° C. (ice/brine bath). Turbo Grignard 1.3M in THF (5.50 mL, 7.14 mmol) is then added in one portion and the reaction stirred for 15 minutes at −8° C. Butyraldehyde (0.698 μL, 7.79 mmol) is then charged in another flask and the preformed anion is added over the aldehyde/THF (4 mL) via canula and then, reaction allowed to warmed at room temperature overnight under magnetic stirring. Ammonium chloride (sat. aq.) added to the mixture. Extracted 3× with Ethyl Acetate. Combined organic layers washed with water (1×), with brine (1×), dried over sodium sulfate, filtered and concentrated to afford the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/Heptane) provide the title compound as a yellow oil (1.33 g, 80.6%). 1H NMR (400 MHz, DMSO-d6) δ 0.83 (t, J=7.41 Hz, 3H) 1.18-1.34 (m, 2H) 1.46-1.57 (m, 2H) 4.52-4.58 (m, 1H) 5.37 (d, J=4.88 Hz, 1H) 7.56 (dd, J=8.58, 1.95 Hz, 1H) 7.79 (d, J=8.39 Hz, 1H) 7.81 (d, J=2.15 Hz, 1H); MS (M): 255.

Workup

  1. customreaction allowed
  2. temperatureto warmed at room temperature overnight under magnetic stirring
  3. extractionExtracted 3× with Ethyl Acetate
  4. washCombined organic layers washed with water (1×), with brine (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude material
  9. customPurification by silica gel flash chromatography (Ethyl Acetate/Heptane)

Sources & evidence

ORD record
ord-d8d9f290cf81496796a0e409d1b4c6d9
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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