3,4-Dichlorobenzaldehyde → HCID 74058494, compound

HRID 1836544Notes

Reaction equation

HRID 1836544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.Cl.[NH2:12][OH:13].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>>[C:19]([O:18][C:16](=[O:17])[CH2:15][O:13][N:12]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 79177tert-Butyl bromoacetateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 74058494HCID 74058494, compound

Procedure

Condensation of 3,4-dichlorobenzaldehyde with hydroxylamine hydrochloride followed by reaction with tert-butyl bromoacetate using a procedure similar to the one described for the preparation of compound 6-A gave the title oxime ether as a clear oil after chromatography on silica gel (elution dichloromethane-hexane 1:1) (94% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.52 (9H, s, t-Bu), 4.63 (2H, s, OCH2), 7.41 (1H, dd, J=1.9 Hz and J=8.6 Hz, aromatic), 7.47 (1H, d, J=8.6 Hz, aromatic), 7.71 (1H, d, J=1.9 Hz, aromatic), 8.13 (1H, s, CH).

Sources & evidence

ORD record
ord-0d81d88bb47941bc852d15bf2956de4f
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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