Water → 2-Bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester
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
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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-463291f560964626a175027b3b6051fe
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669234B2
Reaction notes
Loading…