Aniline → Methyl 3-anilino-5-bromobenzoate
Reaction equation
COC(=O)c1cc(Br)cc(Br)c1.Nc1ccccc1>CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COC(=O)c1cc(Br)cc(Nc2ccccc2)c1Participants
7
Conditions
- Temperature
- 110 °C
Procedure
aniline (0.380 g, 4.08 mmol), methyl 3,5-dibromobenzoate (1.000 g, 3.40 mmol), Pd(OAc)2 (0.076 g, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.295 g, 0.51 mmol) and CESIUM CARBONATE (1.663 g, 5.10 mmol) were stirred in toluene (10 mL) and degassed with nitrogen for 15 minutes. The mixture was then heated at 110 °C under nitrogen for 24 hours. No evidence of any significant amount of product (ester or acid) therfore abandaned.
Sources & evidence
- ORD record
- ord-c6d710180f5249588ab02dc546a2ae67
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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