Tetraethyltin → 3-Ethyl-4-methoxybenzonitrile
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[CH2:12]([Sn](CC)(CC)CC)[CH3:13].[Cl-].[Li+]>CN(C=O)C.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:12]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6])[CH3:13]Participants
6
Conditions
- Temperature
- 135 °C
Procedure
To a solution of 3-bromo-4-methoxybenzonitrile (12-1, 0.3 g, 1.42 mmol) in DMF (14 mL) was added tetraethyltin (0.56 mL, 2.83 mmol), bis(tri-t-butylphosphine) palladium(0) (0.072 g, 0.141 mmol), and lithium chloride (0.18 g, 4.24 mmol) and the system was heated to 135° C. for 30 minutes in a microwave reactor. The mixture was partitioned between saturated NaHCO3 and EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 10% EtOAc in hexanes) to yield the desired product (12-2) as a clear oil. ESI+MS [M+H]+ C10H11NO: 162.1 found, 162.2 required.
Workup
- customThe mixture was partitioned between saturated NaHCO3 and EtOAc
- washThe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by gradient elution on silica gel (0 to 10% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-828637ebf62a41ccad3e97ffe00a938d
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003797B2
Reaction notes
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