Chloroform → 7-(2-Hydroxyethyl)-2-nitro-3-phenylbenzofuran

HRID 262215Notes

Reaction equation

Br[C:2]1[O:3][C:4]2[C:16]([CH2:17][CH2:18][OH:19])=[CH:15][CH:14]=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C(O)=O)CC=CCC1.C(Cl)(Cl)Cl.[N+:33]([O-:38])([N+]([O-])=O)=[O:34]>O>[OH:19][CH2:18][CH2:17][C:16]1[C:4]2[O:3][C:2]([N+:33]([O-:38])=[O:34])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred mixture of 28.6 g. (0.0904 mole) of 2-bromo-7-(2-hydroxyethyl)-3-phenylbenzofuran (the product of step A, Example 5) and 15.1 g. of 4-cyclohexenecarboxylic acid in 250 ml. of chloroform is added dropwise 10.8 g. (0.118 mole) of dinitrogen tetraoxide in 30 ml. of chloroform. After 16 hours, 7 g. of dinitrogen tetraoxide and 5 g. of 4-cyclohexenecarboxylic acid in 30 ml. of chloroform are added, and the mixture is heated at 45° C. for four hours. Water is added to the mixture, the chloroform layer is separated and washed with water, then thrice with sodium bicarbonate solution, thrice with water, once with saturated sodium chloride solution and dried. Evaporation provides a yellow residue. Thin layer chromatographic analysis shows two main products. This residue is recrystallized from 50/50 ethanol/water, then again from carbon tetrachloride to yield 7-(2-hydroxyethyl)-2-nitro-3-phenylbenzofuran as a yellow solid, m.p. 133.5°-136° C.

Workup

additionTo a stirred mixture of 28.6 g
customthe chloroform layer is separated
washwashed with water
dry with materialthrice with sodium bicarbonate solution, thrice with water, once with saturated sodium chloride solution and dried
customEvaporation
customprovides a yellow residue
customThis residue is recrystallized from 50/50 ethanol/water

Sources & evidence

ORD record: ord-6ef475404930449eabcfa783d1aacdca
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153716

Reaction notes

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