Water → 6-Methoxy-2-nitro-3-phenylbenzofuran

HRID 2397880Notes

Reaction equation

HRID 2397880 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCC(C(O)=O)CC=1.[N+:28]([O-:33])([N+]([O-])=O)=[O:29].O>C(O)(=O)C.C(OCC)C>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:2]([N+:28]([O-:33])=[O:29])[O:3][C:4]=2[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 214367902-Bromo-6-methoxy-3-phenylbenzofuran

Product 1

HCID 214367936-Methoxy-2-nitro-3-phenylbenzofuran

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 33.9 g (0.112 mole) of 2-bromo-6 -methoxy-3-phenylbenzofuran in 1 l. of acetic acid is added 21.2 g (0.168 mole) of cyclohexene-4-carboxylic acid, then 15.5 g (0.168 mole) of dinitrogen tetraoxide in 20 ml of acetic acid is added dropwise over 1.5 hours. After 3 additional hours the mixture is poured into cold water to give a yellow gum. The mixture is treated with diethyl ether and the solid residue is collected by filtration. This residue is recrystallized from aqueous ethanol, cyclohexane and ethanol to provide yellow solid 6-methoxy-2-nitro-3-phenylbenzofuran, m.p. 100°-106° C., containing 20 % 7-bromo-6-methoxy-2-nitro-3-phenylbenzofuran.

Workup

  1. customto give a yellow gum
  2. filtrationthe solid residue is collected by filtration
  3. customThis residue is recrystallized from aqueous ethanol, cyclohexane and ethanol

Sources & evidence

ORD record
ord-ac63be3ee73145bcaae49f0a84719245
Source dataset
uspto-grants-1977_05
Patent number
US04022908

Reaction notes

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