Benzyl Bromide → 1-(3-Nitro-4-phenylmethoxyphenyl)ethanone

HRID 2425018Notes

Reaction equation

HRID 2425018 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-hydroxy-3-nitro-phenyl)-ethanone was treated with benzyl bromide in the presence of K2CO3 in DMF, and processed as reported in the synthesis of example 20a to obtain the crude product which was purified using flash chromatography (silica gel, 5% CH3CN in chloroform). Yield, 94%; mp, 132° C.; MS (CI): 300 (M++29), 272 (M++1), 91; analysis: C15H13NO4 requires, C, 66.42; H, 4.83; N, 5.16. found; C, 66.58; H, 4.52; N, 5.30%.

Workup

  1. customas reported in the synthesis of example 20a

Sources & evidence

ORD record
ord-df808e0f648247e7885d7964c8b9c623
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

Loading…