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1,4-Dibromobenzene → Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate

HRID 518
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인쇄 미리보기

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HRID 518 반응식
Brc1ccc(Br)cc1.CCOC(=O)C1CCNCC1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CCOC(=O)C1CCN(c2ccc(Br)cc2)CC1
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참가 물질

7

반응물 2

HCID 78041,4-DibromobenzeneHCID 70770Ethyl 4-piperidinecarboxylate

생성물 1

HCID 71093667Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate수율 59.1%

시약·촉매·용매 4

HCID 23676156Sodium t-butoxide시약HCID 634876Binap, (A+-)-촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

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온도
85 °C

실험 절차

A suspension of ethyl piperidine-4-carboxylate (3.27 mL, 21.20 mmol), 1,4-dibromobenzene (5 g, 21.20 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.485 g, 0.53 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.990 g, 1.59 mmol) and Sodium Tert-Butoxide (2.444 g, 25.43 mmol) in anhydrous toluene (60 mL) was stirred at 85 °C under nitrogen for 16 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford ethyl 1-(4-bromophenyl)piperidine-4-carboxylate (3.91 g, 59.1 %) as a yellow oil.

출처 및 근거

ORD 기록
ord-6d4c20d55c834a949848dd34c3fa431d
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
출처 보기

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