Phenol → HCID 86664211, compound

HRID 1184446Notes

Reaction equation

HRID 1184446 reaction equation
[F: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]>>[F: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 18452164HCID 18452164, compound

Product 1

HCID 86664211HCID 86664211, compound

Procedure

Using 3-fluoro-4-hydroxy-5-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure of alkylation of substituted 2-nitrophenols gives a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=6.57 Hz, 3H) 3.66 (s, 3H) 5.27 (qd, J=6.78, 1.64 Hz, 1H) 8.10-8.18 (m, 1H) 8.31-8.38 (m, 1H) 9.95 (d, J=2.02 Hz, 1H). ESI-MS: m/z 272.1 (M+H)+.

Workup

  1. customgives a yellow solid

Sources & evidence

ORD record
ord-3a2c0479080e4509a2a469325f9fd18d
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

Loading…