Hydrochloric Acid → 2,6-Dichloro-benzaldehyde chloro-oxime

HRID 250221Notes

Reaction equation

HRID 250221 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1C=O.ClN1C(=[O:17])CCC1=O.[ClH:19].C[N:21]([CH:23]=O)C>>[Cl:19][O:17][N:21]=[CH:23][C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 67372,6-DichlorobenzaldehydeHCID 31398Chlorosuccinimide

Product 1

HCID 866424822,6-Dichloro-benzaldehyde chloro-oxime

Procedure

To a solution of 2,6-dichloro-benzaldehyde (7.6 g, 40 mmol) in DMF (56 mL) is added N-chlorosuccinimide (5.9 g, 44.0 mmol) followed by a catalytic amount of HCl gas. The reaction mixture is stirred overnight. The reaction mixture is partitioned between ether and water. The layers are separated and the ether layer is washed with brine and dried over sodium sulfate. The ether layer is filtered and the solvent is removed under reduced pressure to yield the crude product. The crude product is chromatographed using a gradient of 10% ethyl acetate in hexanes to 15% ethyl acetate in hexanes to yield the title compound. 1H-NMR (400 MHz, CDCl3) δ 8.76 (b, 1H), 7.38-7.26 (m, 3H).

Workup

  1. customThe reaction mixture is partitioned between ether and water
  2. customThe layers are separated
  3. washthe ether layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe ether layer is filtered
  6. customthe solvent is removed under reduced pressure
  7. customto yield the crude product
  8. customThe crude product is chromatographed

Sources & evidence

ORD record
ord-1cd29cb2eb754761b272e586d68b8d02
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

Loading…