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

HRID 1060337Notes

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-c0ba09b3303a48118b07f84f6b776303
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521754B2

Reaction notes

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