Tetraethyltin → Methyl 5-chloro-2-ethylbenzoate

HRID 924674Notes

Reaction equation

HRID 924674 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[Li+].[CH2:15]([Sn](CC)(CC)CC)[CH3:16]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:2]([CH2:15][CH3:16])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 11704TetraethyltinHCID 280500Methyl 2-Bromo-5-chlorobenzoateHCID 433294Lithium Chloride

Product 1

HCID 59382453Methyl 5-chloro-2-ethylbenzoateYield 55%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-bromo-5-chlorobenzoate (1.0 g, 4 mmol), lithium chloride (490 mg, 11.58 mmol), tetraethyltin (0.81 mL, 4.1 mmol) and bis(triphenylphosphine)-palladium(II)chloride (100 mg, 0.13 mmol) were combined in DMF (20 mL) and heated at 100° C. for 5 h. Solvent was removed at reduced pressure and the residue was diluted with water and EtOAc. The organic layer was separated, washed with water, dried over sodium sulfate and concentrated. Column chromatography on silica gel (0 to 10% EtOAc/hexane) provided the title compound (435 mg, 55%).

Workup

  1. customSolvent was removed at reduced pressure
  2. additionthe residue was diluted with water and EtOAc
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37111638b31e48d8be3ca34f6c7d5614
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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