Methyl 4-bromo-2-nitrobenzoate → HCID 59164467, compound

HRID 906599Notes

Reaction equation

HRID 906599 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[CH2:15](C([Sn])=C(CCCC)CCCC)[CH2:16]CC>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:15]=[CH2:16])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 2

HCID 18350461Methyl 4-bromo-2-nitrobenzoateHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 59164467HCID 59164467, compoundYield 102.8%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-nitro-benzoic acid methyl ester (1 g, 3.85 mmol) in dioxane (5 mL) were added tributylvinyltin (1.7 mL, 5.76 mmol) and Pd(Ph3P)2Cl2 (275.4 mg, 0.385 mmol). The reaction mixture was stirred at 80° C. for 18 h, was cooled to r.t. and was diluted with EtOAc. After removal of the precipitate by filtration, the solution was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes→1:1 hexanes:EtOAc) to provide the title compound (820 mg, 100%, 97% purity by HPLC) as a yellow oil. ESI-MS: m/z 208.2 [M+H]+, rt 5.14 min.

Workup

  1. temperaturewas cooled to r.t.
  2. customAfter removal of the precipitate
  3. filtrationby filtration
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, hexanes→1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-b8ece99cec3d4c6fb70763bc2d682a30
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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