6-(4-Bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one → [2,6-Dibromo-4-(hydroxymethyl)phenyl]acetonitrile

HRID 271192Notes

Reaction equation

HRID 271192 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([Br:10])[C:7]=1[CH2:8]Br.BrCC1C=C(Cl)C(CC2C=C(C(C)C)[C:23](=O)[NH:24]N=2)=C(Cl)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([Br:10])[C:7]=1[CH2:8][C:23]#[N:24]

Participants

3

Reactant 2

HCID 598344466-(4-Bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-oneHCID 59834487[3,5-Dibromo-4-(bromomethyl)phenyl]methanol

Product 1

HCID 59834476[2,6-Dibromo-4-(hydroxymethyl)phenyl]acetonitrileYield 78%

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

Workup

  1. customThis compound was prepared by a similar method to
  2. customThe product was purified by flash chromatography
  3. washeluted with a gradient of 3:1 to 1:1 hexanes
  4. customThe desired fractions were collected
  5. concentrationconcentrated under vacuum
  6. customto afford a solid which
  7. customwas dried under high vacuum

Sources & evidence

ORD record
ord-7edb2ff4781b4237b01153158945a65f
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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