Reaction #2286321

Reaction equation

(3,5-dibromo-4-bromomethyl-phenyl)-methanol

(3,5-Dibromo-4-bromomethyl-phenyl)-methanol

6-(4-bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one

6-(4-Bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one

→

acetonitrile

Yield 78.0%

(2,6-Dibromo-4-hydroxymethyl-phenyl)-acetonitrile

Yield 78.0%

Conditions

Workup

1. 1
   OtherThis compound was prepared by a similar method to
2. 2
   OtherThe product was purified by flash chromatography
3. 3
   Washeluted with a gradient of 3:1 to 1:1 hexanes
4. 4
   OtherThe desired fractions were collected
5. 5
   Concentrationconcentrated under vacuum
6. 6
   Otherto afford a solid which
7. 7
   Otherwas dried under high vacuum

Procedure

This compound was prepared by a similar method to that described in Example 14, Step 5 except that (3,5-dibromo-4-bromomethyl-phenyl)-methanol (58) was used in place 6-(4-bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one (54). The product was purified by flash chromatography using silica gel eluted with a gradient of 3:1 to 1:1 hexanes:ethyl acetate. The desired fractions were collected and concentrated under vacuum to afford a solid which was dried under high vacuum to afford 2,6-dibromo-4-hydroxymethyl-phenyl)-acetonitrile (59) (78%) as a yellow solid; EI(+)-HRMS m/z calcd for C9H7Br2NO (M 302.8894, found 302.8881. MW=304.9702, Exact Mass=302.8894

Source