Carbon tetrabromide → HCID 16107231, compound

HRID 1958641Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7])=O.[C:16](Br)(Br)([Br:18])[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:17][C:16]([Br:18])=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 3-formyl-4-nitrobenzoate (23.7 mmol) and carbontetrabromide (8.66 g, 26.1 mmol) in dichloromethane (50 ml) was added dropwise a solution of triphenylphosphine (12.44 g, 47.5 mmol) in dichloromethane (50 ml) at 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h at 0° C. and then allowed to warm to room temperature. A small amount of white solid was formed. The solution was concentrated to 30 mL and then filtered. The organic solvent was concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, 10% EtOAc in hexanes as eluent) to afford methyl 3-(2,2-dibromovinyl)-4-nitrobenzoate was obtained as a light tan solid (32 g, 74%); 400 M Hz 1H NMR (CDCl3) 8.26 (br s, 1H), 8.12-8.18 (m, 2H), 7.75 (s, 1H), 3.98 (s, 3H).

Workup

temperatureto warm to room temperature
customA small amount of white solid was formed
concentrationThe solution was concentrated to 30 mL
filtrationfiltered
concentrationThe organic solvent was concentrated under reduced pressure
customThe crude product was purified by flash column chromatography (SiO2, 10% EtOAc in hexanes as eluent)

Sources & evidence

ORD record: ord-09fa171092af430f8cec58c80310dcc4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410144B2

Reaction notes

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