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5th December 2016 @ 10:53

AT-1-012

Synthesis of 4-(Pyrrolidin-1-yl)benzaldehyde from 4-Fluorobenzaldehyde and Pyrrolidine via SNAr using sonication

 reaction scheme

 

 

Reagent

Eq

Mw

mmol

w/vol

4-Fluorobenzaldehyde

1

124.11

2.2

0.21ml

Pyrrolidine

3

71.12

2.2

0.18ml

DMSO

-

78.13

-

2ml

K2CO3

1.5

138.21

2.2

0.304g

 

Experimental Procedure

 

Pyrrolidine (0.18ml, 2.2mmol) was added to DMSO (2ml), in a round bottom flask and then anhydrous K2CO3 (0.304g, 2.2mmol) and 4-Fluorobenzaldehyde (0.21ml, 2.2mmol) were added sequentially. The round bottom flask was placed into a sonication machine and turned on and left to react for 15 minutes.

After 15 minutes, a TLC was taken from the mixture (5:3 Pet. Ether: Diethyl ether), this showed the reaction hadn’t moved far due to the large amounts of starting material present in the product. The reaction was put on for a further 45 minutes and a TLC was taken after this time, but it showed almost no change.

IMG_2615.png

The reaction to synthesise 4-(Pyrrolidin-1-yl)benzaldehyde using sonication didn’t produce results, so the previous experiment using SNAr reaction without sonication was decided to be used as the route of synthesis for 4-(Pyrrolidin-1-yl)benzaldehyde as it produced a good yield to move forward. No successfull yield was produced so no NMR data was taken as it was deemed unnecessary.

Reference:

  1. Magdolen, Peter, Tetrahedron, 2001 ,  vol. 57,  # 22  p. 4781 – 4785
  2. Organic-chemistry, sonochemistry, http://www.organic-chemistry.org/topics/sonochemistry.shtm, accessed 16th Oct 2016

 

 

 

 

 

Attached Files
sNAR reaction sonication.png
IMG_2615.png