Morpholine → Dimethyl 5-morpholinoisophthalate
Reaction equation
C1COCCN1.COC(=O)c1cc(Br)cc(C(=O)OC)c1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)c1cc(C(=O)OC)cc(N2CCOCC2)c1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
To a solution of dimethyl 5-bromoisophthalate (10 g, 36.62 mmol) in toluene (100 mL) where BINAP (2.5 g, 4.01 mmol), morpholine (4.4 g, 50.50 mmol), CESIUM CARBONATE (18 g, 55.25 mmol) and PALLADIUM(II) ACETATE (0.9 g, 4.01 mmol) added. The solution was heated to reflux under inert atm for 14h. The silvent was filtered and the filtrate was concentrated. The residue was purified by column chropmatography (Hep:EA) 1:1 to give dimethyl 5-morpholinoisophthalate (8.00 g, 78 %)
Sources & evidence
- ORD record
- ord-ff0eb93bbb4b45cdb3807c4588dd206f
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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