1,3-Dibromopropane → 5,6,7,8-Tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene

HRID 2393298Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[N+:23]([C:14]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[CH:21]=[CH:22][C:13]=1[O:12][CH2:10][CH2:9][CH2:8][Br:7])([O-:25])=[O:24]

Participants

Conditions

Temperature: 70 °C

Procedure

N,N-dimethylformamide (180 ml), potassium carbonate (37.8 g, 0.273 mol), and 1,3-dibromopropane (93 ml, 0.916 mol) were added to 2-hydroxy-5,6,7,8-tetrahydro-1-nitronaphthalene (17.6 g, 0.091 mol) and the mixture was stirred at 70° C. for 4 hours. The precipitated salts were removed by filtration, and then the solvent was evaporated and the residue was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20) to give 5,6,7,8-tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene (19.4 g).

Workup

customThe precipitated salts were removed by filtration
customthe solvent was evaporated
extractionthe residue was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record: ord-c4cb0050bb6f4f3f81ba1e388453dfb5
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807860

Reaction notes

Loading…