Water → 1-Iodo-3-methoxy-5-nitrobenzene

HRID 2308560Notes

Reaction equation

[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:14][O-:15].[Na+].O>CO>[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:15][CH3:14])[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

1-Iodo-3,5-dinitrobenzene (1.8 g, 6.1 mmol) are dissolved in methanol (12 ml) and treated with a solution of sodium methoxide in methanol (5.4M, 1.2 ml). The mixture is then stirred at 65° C. for 52 h. After cooling to ambient temperature, water (50 ml) is added and the mixture extracted three times with ethyl acetate (50 ml). The combined organic layers are extracted with brine (100 ml), dried and evaporated to dryness. Flash chromatography (silica, eluent ethyl acetate/cyclohexane 1:1) affords the product (1.7 g, 99%) as light yellow solid. MS: m/e=279 (M+).

Workup

temperatureAfter cooling to ambient temperature
extractionthe mixture extracted three times with ethyl acetate (50 ml)
extractionThe combined organic layers are extracted with brine (100 ml)
customdried
customevaporated to dryness

Sources & evidence

ORD record: ord-bec7ea46e7784855a45e6a761d8fa853
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835732B2

Reaction notes

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