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20th September 2016 @ 04:26


3,4-difluorobenzaldehyde (2.00 g, 14.1 mmol, 1.00 equiv.) was dissolved in anhydrous ether (28 mL) and then stirred at 0 ˚C. MeMgBr (4.74 mL, 14.2 mmol, 1.01 equiv, 3.0 M in THF) (colourless to pale yellow soln) and the reaction mixture stirred at 0˚C for 5 min and then allowed to warm to rt and stirred for 30 mins.

TLC showed no SM (30% EtOAc in Hexane)

30%EtOAc in Hexane.jpeg

Reaction mixture cooled to 0 ˚C and then a saturated solution of 1 M HCl (20 mL) added dropwise with stirring (no vigourous reaction). Volatiles were removed in vacuo to give a yellow ppt. Reaction mixture partioned between EtOAc (40 mL) and a saturated solution of ammonium chloride (40 mL) and then layers separated. Aqueous washed with EtOAc (2 x 30 mL) and then combined organic washed with water (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated to give a pale pink liquid (2.00 g, 12.7 mmol, 90% crude yield) which was used as crude in the subsequent Swern Oxidation. 



200 MHz NMR in CDCl3

AEW 315-1 Proton.png
AEW 315-1 Proton.jcamp
AEW 315-1 Proton.mnova








Attached Files
30%EtOAc in Hexane.jpeg
AEW 315-1 product.png
AEW 315-1.png
AEW 315-1.cdxml
AEW 315-1.rxn
AEW 315-1 Proton.png
AEW 315-1
AEW 315-1 Proton.mnova