Phenol → HCID 86664210, compound

HRID 1184430Notes

Reaction equation

HRID 1184430 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])C=O.[C:13]1([OH:19])C=CC=CC=1.Br[CH:21]([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[F:27][CH:21]([O:1][C:2]1[CH:3]=[CH:4][C:7]([CH:13]=[O:19])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 3

HCID 996PhenolHCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl ester

Product 1

HCID 86664210HCID 86664210, compound

Procedure

Using 3-hydroxy-4-nitrobenzaldehyde as the phenol and ethyl 2-bromo-2-fluoroacetate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (t, J=7.07 Hz, 3H), 4.26-4.38 (m, 2H), 6.83 (d, J=55.8 Hz, 1H), 7.76 (dd, J=8.84, 1.26 Hz, 1H), 8.28 (dd, J=8.59, 2.02 Hz, 1H) 8.54 (d, J=2.02 Hz, 1H), 10.02 (s, 1H). ESI-MS: m/z 272.1 (M+H)+.

Workup

  1. customgives a yellow oil

Sources & evidence

ORD record
ord-1b6c84ec0c864df58bfe067f95ee17e1
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

Loading…