Boron trifluoride etherate → 1-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzene

HRID 2206707노트

반응식

HRID 2206707 반응식
[Br:1][C:2]1[CH:3]=[C:4]([O:19][CH3:20])[C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([O:19][CH3:20])[C:5]=2[Cl:18])=[CH:11][CH:12]=1)[CH3:17]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71110682(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone

생성물 1

HCID 710770511-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzene수율 56.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of compound 61 (4.45 g, 12.6 mmol) in CH2Cl2 (80 mL) was added dropwise triethylsilane (6.00 mL, 37.8 mmol) and boron trifluoride diethyl etherate (4.67 mL, 37.8 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 5 hours at room temperature, the mixture was quenched with aq. saturated K2CO3 solution (30 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 62 (2.40 g, 56%) as colorless oil.

후처리

  1. customthe mixture was quenched with aq. saturated K2CO3 solution (30 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-fe5f7788b6044e809141d00f28f15c92
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371303B2

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