4-Fluorobenzaldehyde → HCID 74058495, compound

HRID 1836501Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[NH2:11][OH:12].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>>[C:18]([O:17][C:15](=[O:16])[CH2:14][O:12][N:11]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Reactant 3

HCID 680234-Fluorobenzaldehyde

HCID 79177tert-Butyl bromoacetate

HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 74058495HCID 74058495, compoundYield 84%

Procedure

Condensation of 4-fluorobenzaldehyde with hydroxylamine hydrochloride followed by reaction with tert-butyl bromoacetate using the same procedure as described for compound 6-A gave the title oxime ether as a clear oil (84% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.52 (9H, s, t-Bu), 4.61 (2H, s, OCH2), 7.08 (2H, m, aromatics), 7.59 (2H, m, aromatics), 8.19 (1H, s, CH).

Sources & evidence

ORD record: ord-7dd4dc060225428b9ae33999c813f166
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

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