Ethyl Acetate → 5-Bromo-2-(2-fluorophenyl)pyridine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:13][CH:14]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Under nitrogen, 39.2 g (0.28 mol) of 2-fluoro-phenylboronic acid, 59.9 g (0.25 mol) of 2,5-dibromopyridine and 2.17 g of tetrakis(triphenylphosphine)palladium were dissolved in 420 ml of ethanol and 840 ml of toluene. 840 ml of a 2 N sodium carbonate solution were added, and the mixture heated to 80° C. for 1 h. Afterwards the mixture was cooled to 5 to 10° C., 800 ml of ethyl acetate were added, and the precipitated salts were separated by filtration. The organic phase of the mother liquor was separated, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness.
Workup
- temperatureAfterwards the mixture was cooled to 5 to 10° C.
- customthe precipitated salts were separated by filtration
- customThe organic phase of the mother liquor was separated
- washwashed with a saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-5021d7b178ce49d89e0cad253662bb14
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188291B2
Reaction notes
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