Tetraethyltin → Methyl 5-chloro-2-ethylbenzoate

HRID 924674노트

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HRID 924674 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-37111638b31e48d8be3ca34f6c7d5614
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283224B2

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