Allyl bromide → 1-(Allyloxymethyl)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene

HRID 1175296노트

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HRID 1175296 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][OH:19].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:24]([O:19][CH2:18][C:3]1[CH:4]=[C:5]([Cl:17])[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[Br:1])[CH:23]=[CH2:22]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 59467877(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

생성물 1

HCID 595576981-(Allyloxymethyl)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene수율 84.8%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매2회

반응 조건

온도
-10 °C

실험 절차

To a solution of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (3.4 g, 10 mmol) in DMF (50 mL) was added NaH (0.8 g, 20 mmol, 60% in miner oil) in portions at −5° C. After being stirred for 1 h at the same temperature, the reaction mixture was cooled to −10° C., TBAI (0.37 g, 1 mmol) and a solution of allyl bromide (1.45 g, 12 mmol) in DMF (10 mL) was added. The reaction mixture was stirred for another 1 h prior to quenching by ice water and extracted 3× with EtOAc. The combined organic layers were washed with brine and then dried over Na2SO4. Concentration gave the crude product, which was purified by silica column chromatography (elution with PE:EtOAc=10:1) to afford the title compound (3.22 g, yield 84.8%).

후처리

  1. stirringThe reaction mixture was stirred for another 1 h
  2. customto quenching by ice water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration
  7. customgave the crude product, which
  8. customwas purified by silica column chromatography (elution with PE:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-8b01a15909f149b8970b8d65b2ab05a1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838498B2

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