1,4-Dibromo-2-nitrobenzene → HCID 67314075, compound

HRID 1012639Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Li]C1C=CC=CC=1.[CH3:19][O:20][C:21]1[CH:37]=[CH:36][C:24]([CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([CH3:35])=[C:31]([CH:34]=2)[CH:32]=[O:33])=[CH:23][CH:22]=1>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:32]([C:31]2[CH:34]=[C:27]([O:26][CH2:25][C:24]3[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:37][CH:36]=3)[CH:28]=[CH:29][C:30]=2[CH3:35])[OH:33])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1,4-dibromo-2-nitro-benzene (5.89 g, 21.00 mmol) in THF (300 ml) was added a solution of PhLi (1.8 M in cyclohexane/diethyl ether 7:3, 12.8 ml, 23.1 mmol) at −110° C. The mixture was stirred at the same temperature for 1 h. Compound 502 (4.45 g, 17.4 mmol) in THF (100 ml) was dropwise added to the mixture. The reaction mixture was then allowed to warm to −78° C. and stirred at the same temperature for 4 h. Afterwards, the reaction mixture was quenched with saturated aqueous solution of NH4Cl. the aqueous phase was extracted once with diethyl ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (petroleum ether/ethyl acetate 5:1), furnishing a reddish foam.

Workup

stirringstirred at the same temperature for 4 h
customAfterwards, the reaction mixture was quenched with saturated aqueous solution of NH4Cl
extractionthe aqueous phase was extracted once with diethyl ether
dry with materialThe combined organic phases were dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (petroleum ether/ethyl acetate 5:1)
customfurnishing a reddish foam

Sources & evidence

ORD record: ord-59bc48d75a2d4f1b860d989360c16bbf
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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