Phenol → HCID 65429217, compound

HRID 1184428Notes

Reaction equation

HRID 1184428 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C1(O)C=CC=CC=1.[CH3:19][O:20][C:21](=[O:25])[CH:22](Br)[CH3:23]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:22]([CH3:23])[C:21]([O:20][CH3:19])=[O:25])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 243644-Bromo-2-nitrophenolHCID 95576Methyl 2-bromopropionate

Product 1

HCID 65429217HCID 65429217, compound

Procedure

Using 4-bromo-2-nitrophenol as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a dark red oil: 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.13 (d, J=2.5 Hz, 1H), 7.80 (dd, J=8.8, 2.5 Hz, 1H), 7.24 (d, J=9.1 Hz, 1H), 5.29 (q, J=6.8 Hz, 1H), 3.68 (s, 3H), 1.52 (d, J=6.6 Hz, 3H). ESI-MS: m/z 305.1 (M+H)+.

Workup

  1. customgives a dark red oil

Sources & evidence

ORD record
ord-86b8c92c6c8844bbb1cf81fffe2815ef
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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