Tetraethyltin → Methyl 5-chloro-2-ethylbenzoate

HRID 924674ノート

反応式

HRID 924674 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 59382453Methyl 5-chloro-2-ethylbenzoate収率 55%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-37111638b31e48d8be3ca34f6c7d5614
出典データセット
uspto-grants-2016_03
特許番号
US09283224B2

反応ノート

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