COS Logo

Synthesis of Fenarimol from 2-butene

An organic synthesis project

November 14, 2019

1 Molecule 05/09/2020
Organic Synthesis
 Define
Fenarimol

Is an agricultural and horticultural fungicide. It

has a 331.2 g/mol Molecular weight, a melting
point of 118oC .

2 Fenarimol 05/09/2020
Organic Synthesis

(2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-
ylmethanol is a member of the class of pyrimidines
that is pyrimidin-5-ylmethanol in which one of the
hydrogens attached to the carbon bearing
the hydroxy group is replaced by a 2-chlorophenyl
group while the other is replaced by a 4-
chlorophenyl group.

It is a tertiary alcohol, a member of

monochlorobenzenes and a member of pyrimidines.
This paper introduce an alternative route for
Feranimol starting from 2-butene.

3 Fenarimol 05/09/2020
Organic Synthesis
 Importance:

 It allows chemist to construct new structures, and

empowers chemists to probe the world in new,
and creative ways.
 Objective:
 Perform an alternate path for the synthesis
of Fenarimol using 2-butene as starting
material.
 Enable students’ to integrate their learning
about organic chemistry.

4 Fenarimol 05/09/2020
Organic Synthesis

 Application

The development and continuous progression of art

in chemistry led numerous application in the
society. The development of synthetic materials is
all rooted to the capability of a chemist to analyze
and re-make the organic material in the laboratory.

5 Fenarimol 05/09/2020
Molecule
 Uses of Fenarimol

Fenarimol is a systemic fungicide, which protects,

cures, and eradicates. It is usually applied to
leaves and moves apoplastically through the leaf
towards the tip. Movement from treated to
untreated leaves is not significant enough to
control disease. Application to roots and seeds
results in translocation to all of the aerial parts of
the plant.

 
6 Fenarimol 05/09/2020
Molecule
 Notable synthesis routes for the molecule

7 Fenarimol 05/09/2020
Synthesis Proper
Conversion of 2-butene to 2-butanol
to Ketone

KOH

,Ether

Aqueous Acid

8 Fenarimol 05/09/2020
Supporting reactions

The conversion of 2-bromobutane requires addition of

KOH to form a secondary alcohol, 2-butanol.

9 Fenarimol 05/09/2020
Supporting reactions

Different combinations of Grignard reaction and

carbonyl compounds are possible. Aqueous acid is
added to the initial Grignard reaction to form an alcohol.

10 Fenarimol 05/09/2020
Synthesis Proper
Attaching 4-chlorobromobenzene to the Ketone
through Grignard reaction

11 Fenarimol 05/09/2020
Supporting reactions

R X : Mg R Mg X R Mg X

Mechanism of the Organometallic reagent (RMgX)

12 Fenarimol 05/09/2020
Synthesis Proper
Attaching 2-Bromopyrimidine thru Organo-lithium
exchange

13 Fenarimol 05/09/2020
Supporting reactions

Mechanism of the Organo-lithium exchange

R—Li

14 Fenarimol 05/09/2020
Synthesis Proper
Attaching 2-chlorobenzene

Ether

15 Fenarimol 05/09/2020
Supporting reactions
Same reagent but different order of step yielding to the same
product
1 2

The isolated part of the two

reactions above.

16 Fenarimol 05/09/2020
Challenges
These are the challenges for the first two
weeks:
1. The challenge that the group faced on
Activity 1 was where to start. It was very
hard to figure out what part of the molecule
should we begin and what technique the
group should use to identify the proper
reaction needed.
2. We also had a problem after converting 2 –
butene to butanone which step should be
done to proceed to the flow of reaction
3. The lack of knowledge about Aromatic
17 compounds. Fenarimol 05/09/2020
Lesson Learned
1. We learned that identifying first the functional groups will make
  
the synthesis easier to break down. Using the knowledge we
have in converting alkenes to ketones, we were able to react
our starting molecule (2-butene) with , and this will add an
alcohol on the double bond and as a final step, we oxidize it
with PCC, and because it results to a secondary alcohol and it’s
going to convert into ketone. At that point, we already
converted 2-butene into 2-butanol to 2-butanone.
2. We tried to react 2-butanone to R-Li to form an organolithium
reagent and react it with /H + resulting to a R-(C=O)-R ketone.
Carbon double bonded to oxygen and an alkyl groups attached
on the carbon.
3. During the first and second week of our synthesis, in our lecture
class we haven’t yet rolled up to discuss aromatic rings, and
aromatic substitution. For that reason, we were having a hard
time to devise the mechanism of the formation of phenyl
groups around the ketone.
18 Fenarimol 05/09/2020
Lesson Learned
4.) On week 04, the group was able to identify
another way of converting alkenes to Ketone
through reacting 2-butene to HBr yielding to
2-bromobutane and adding H2O yielding to a
secondary alcohol, 2-butanol. From this we
can perform a reverse reaction, because we
know that 2-butanol is also created by
combining Grignard reaction and carbonyl
compounds added with aqueous acid results
to an alcohol. From this, 2-butanol will yield
with 2 products, the Ch3Ch2CHO +
Ch3MgBr(Organometalic reagent).
19 Fenarimol 05/09/2020
References
 Wikipedia contributors. (2019, October 19). Fenarimol.
In Wikipedia, The Free Encyclopedia. Retrieved 11:04,
November 10, 2019,
from https://en.wikipedia.org/w/index.php?
title=Fenarimol&oldid=922102759
 National Center for Biotechnology Information. PubChem
Database. Fenarimol, CID=43226,
https://pubchem.ncbi.nlm.nih.gov/compound/Fenarimol
(accessed on Nov. 10, 2019).
 Althaus, W.A. (1984) A comparative photodegradation
study conducted with carbinol-labelled, o-chlorophenyl-
labelled, p-chlorophenyl- labelled, and mixed-labelled 14C
fenarimol. DowElanco Company report.
http://www.inchem.org/documents/jmpr/jmpmono/v95pr20.
htm

20 Fenarimol 05/09/2020