1,1-Dibromoethane → HCID 18789849, compound

HRID 1106884Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH:5]=1)([O-:3])=[O:2].[Br:16][CH:17](Br)[CH3:18].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][CH2:17][Br:16])=[C:6]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 70 °C

Procedure

4-Nitro-2-(1H-pyrrol-1-yl)phenol (2.3 g, 112.6 mmol) and dibromoethane (29.1 ml, 337.8 mmol) were dissolved in DMF (200 ml) and, after adding K2CO3 (18.68 g), the solution was stirred at 70° C. for 1 h. Thereafter, an aqueous solution of 10% sodium hydroxide was added to the reaction solution to render it basic up to a pH of about 10, followed by three extractions with ethyl acetate. The organic solvent layers were combined and dried with magnesium sulfate, followed by evaporation of the solvent. The resulting residue was purified by being subjected to column chromatography on silica gel using a 3:1 solvent system of n-hexane and ethyl acetate as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end product 4-nitro-2-(1H-pyrrol-1-yl)phenoxy-2-bromoethane (15.8 g).

Workup

extractionfollowed by three extractions with ethyl acetate
dry with materialdried with magnesium sulfate
customfollowed by evaporation of the solvent
customThe resulting residue was purified
additionThe fractions containing the product
customwere collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-8926fc2321d44250943b245532f765e7
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057358

Reaction notes

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