Water → 2-Bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester

HRID 2038945

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][C:5]=1[Br:11].C([Sn](CCCC)(CCCC)[CH:18]=[CH:19][O:20]CC)CCC.O.C1C(=O)N([Br:39])C(=O)C1>O1CCOCC1.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:12])[C:4]1[CH:9]=[C:8]([C:19](=[O:20])[CH2:18][Br:39])[CH:7]=[CH:6][C:5]=1[Br:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 2-bromo-5-iodo-benzoic acid methyl ester (4.33 g, 12.7 mmol) and tributyl(ethoxyvinyl)stannane (4.79 g, 13.3 mmol) in dioxane (56 ml) was added PdCl2(PPh3)2 (322 mg). The mixture was heated at 80° C. for 17 hours and was cooled to 0° C. Water (19 ml) was added, followed by slow addition of NBS (2.33 g, 12.9 mmol) over 10 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc=2/1) gave 2-bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester (3.48 g).

Workup

temperaturewas cooled to 0° C
customthe solvent was removed under reduced pressure
additionThe mixture was diluted with EtOAc
washwas washed with water and brine
dry with materialdried with sodium sulfate
concentrationConcentration and purification by flash column chromatography (hexane/EtOAc=2/1)

Sources & evidence

ORD record: ord-67adc994556c4aba8e01c7e5f3349041
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575118B2

Linked notes

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