Reaction #312582

Reaction equation

2,4-difluoroacetophenone

trimethyl ortho-formate

sodium hydrogen carbonate

→

1-(1,1-dimethoxyethyl)-2,4-difluorobenzene

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherreacted at 40° C. to 45° C. for 2 hours
3. 3
   Extractionwas then extracted with ethyl acetate
4. 4
   WashAn extract was washed with water
5. 5
   Otherdried on Na2SO4
6. 6
   ConcentrationThen, ethyl acetate was concentrated

Procedure

In a solution composed of 15.7 g of 2,4-difluoroacetophenone, 35 g of trimethyl ortho-formate and 15 g of methanol, 0.96g of p-toluenesulfonic acid was added, and reacted at 40° C. to 45° C. for 2 hours. This was added to an aqueous solution of 5% by mass sodium hydrogen carbonate, which was then extracted with ethyl acetate. An extract was washed with water, and dried on Na2SO4. Then, ethyl acetate was concentrated to yield 18.2 g of 1-(1,1-dimethoxyethyl)-2,4-difluorobenzene. It was confirmed that the 1-(1,1-dimethoxyethyl)-2,4-difluorobenzene had NMR data of (CDCl3, δppm) 1.62 (s, 3H), 3.9 (s, 6H), 6.74-6.9 (m, 2H), 7.56-7.7 (m, 1H) by NMR (supplied from Varian Technologies Japan Limited).

Source