Phenol → HCID 86664208, compound

HRID 1184424Notes

Reaction equation

HRID 1184424 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[O:6].C1(O)C=CC=CC=1.[CH3:21][O:22][C:23](=[O:27])[CH:24](Br)[CH3:25]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:10][CH:24]([CH3:25])[C:23]([O:22][CH3:21])=[O:27]

Participants

4

Reactant 3

HCID 996PhenolHCID 95576Methyl 2-bromopropionateHCID 18452163HCID 18452163, compound

Product 1

HCID 86664208HCID 86664208, compound

Procedure

Using 3-chloro-4-hydroxy-5-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a light yellow oil: 1H NMR (DMSO-d6, 400 MHz): δ ppm 9.98 (s, 1H), 8.43 (d, J=1.8 Hz, 1H), 8.35 (d, J=2.0 Hz, 1H), 5.08-5.15 (m, 1H), 3.62 (s, 3H), 1.57 (d, J=6.8 Hz, 3H). ESI-MS: m/z 328.1 (M+H)+.

Workup

  1. customgives a light yellow oil

Sources & evidence

ORD record
ord-f83f34d9b070460a8cad0ab828ca3a28
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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