Phenol → HCID 66717340, compound

HRID 1184490Notes

Reaction equation

HRID 1184490 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1.C1(O)C=CC=CC=1.[CH3:23][O:24][C:25](=[O:29])[CH:26](Br)[CH3:27]>>[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[C:5]([O:12][CH:26]([CH3:27])[C:25]([O:24][CH3:23])=[O:29])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 95576Methyl 2-bromopropionateHCID 510579691-(5-Bromo-2-hydroxy-3-nitrophenyl)propan-1-one

Product 1

HCID 66717340HCID 66717340, compound

Procedure

Using 1-(5-bromo-2-hydroxy-3-nitrophenyl)propan-1-one as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted 2-nitrophenols gives the title compound as a gold oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.10 (m, 3H) 1.44 (d, J=6.82 Hz, 3H) 3.00-3.12 (m, 2H) 3.59 (s, 3H) 4.56 (q, J=6.82 Hz, 1H) 8.07 (d, J=2.53 Hz, 1H) 8.34 (d, J=2.53 Hz, 1H). ESI-MS: m/z 361.1 (M+H)+.

Sources & evidence

ORD record
ord-aaf3cb518272485eb100d8c0150151f8
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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