Ethyl bromoacetate → Ethyl 2-(2-methoxy-4-nitrophenoxy)acetate

반응식

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

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실험 절차

The product was prepared by the alkylation of 4-nitro-2-methoxyphenol (10.0 g, 0.059 mol) with ethyl bromoacetate (10.0 g, 0.06 mol) in acetonitrile (50 mL) in the presence of potassium carbonate (8.0 g) to afford 14.33 g (95%) of ethyl 4-nitro-2-methoxyphenoxyacetate as a yellow solid, m.p. 87°-88° C., after recrystallization from tert-butylmethyl ether; hydrogenation of the latter (13.08 g, 0.051 mol) in THF (125 mL)/ethanol (125 mL) in the presence of 10% Pd/C (1.0 g) to afford 11.5 g (100%) of ethyl 4-amino-2-methoxyphenoxyacetate as a pink oil; and then treatment of the latter (11.5 g, 0.051 mol) in CH2Cl2 (100 mL) with pyridine (10 mL), followed by methanesulfonyl chloride (6.43 g, 0.056 mol) to afford 12.328 g (79.6%) of N-[4-(ethoxycarbonylmethoxy)-3-(methoxy)phenyl]methanesulfonamide, m.p. 118°-119° C., after purification by treatment with charcoal and filtration through silica eluting with ethyl acetate.