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4th December 2013 @ 22:56

Zinc Chloride was purified by refluxing in thionyl chloride (thanks Kat Badiola!)

 

ZnCl2 (960 mg, 7.0 mmol) was weighed into an oven-dried flask under Ar. 3,4-Difluorobenzaldehyde (1 g, 7.0 mmol) was dissolved in CH2Cl2 (6 mL) and added at 0 ˚C  and then TMSCN (700 mg, 0.9 mL, 7.0 mmol) was added at 0 ˚C and the reaction mixture stirred at 0 ˚C for 30 minutes. Still SM. Stirred in ice bath whilst slowing warming to 10 ˚C for 3.5 h. TLC, still SM, product and assumed hydroxy side product A

Removed from ice bath and allowed to stir whilst reaching room temperature for 2.5 hours. Still SM so stirred overnight. The reaction mixture was then poured over water (12 mL) , extracted with EtOAc (3 x 20 mL), dried over MgSO4, filtered and evaporated to yield a straw coloured oil. Stored in freezer under Ar over the weekend. 

NMR shows 0.1:1:0.4 SM:sideprod A: product - 1.38 g pale brown oil, submitted crude to AEW 102-3

Data:

AEW 94-8 (10% EtOAc in hexane).jpg
AEW 94-8 proton.pdf
 
AEW 94-8 crude.zip

Hazard and Risk Assessment:

On 5 x the scale (1 g) - reaction performed in isolated fumehood with additional sign on hood exterior.

HIRAC AEW 94-6.pdf
 

InChi:

InChI=1S/C7H4F2O/c8-6-2-1-5(4-10)3-7(6)9/h1-4H

goes to

InChI=1S/C11H13F2NOSi/c1-16(2,3)15-11(7-14)8-4-5-9(12)10(13)6-8/h4-6,11H,1-3H3

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Attached Files
side product.png
AEW 94-8 (10% EtOAc in hexane).jpg
AEW 94-8 proton.pdf
AEW 94-8 crude.zip