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Aluminum(III) Chloride → (3-bromonaphthalen-2-yl)methanol

HRID 2390891
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HRID 2390891 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].C([O:13][C:14]([C:16]1[C:25]([Br:26])=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)=O)C.O.N>O1CCCC1>[Br:26][C:25]1[C:16]([CH2:14][OH:13])=[CH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2
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참가 물질

6

반응물 4

HCID 6451240Aluminum(III) ChlorideHCID 12896473Azane;hydrateHCID 21226445Aluminium lithium hydrideHCID 68549726HCID 68549726, 화합물

생성물 1

HCID 264948(3-bromonaphthalen-2-yl)methanol수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

To the mixture of lithium aluminum hydride (430 mg, 9.0 mmol) and tetrahydrofuran (15 ml) under nitrogen atmosphere, aluminum chloride (1.7 g, 13 mmol) was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 1 hour. Subsequently, 3-bromo-naphthalene-2-carboxylic acid ethyl ester (500 mg, 1.8 mmol) was added to the reaction mixture at 0° C. (an outer temperature), and the reaction mixture was stirred at the same temperature for 1.5 hours. 28% ammonia water was added to the reaction mixture, followed by filtration with Celite. The solvents were evaporated under reduced pressure from the filtrate, and then the obtained residue was purified with NH-silica gel column chromatography (heptane:ethyl acetate=3:1), thereby obtaining the entitled compound (280 mg, 67%).

후처리

  1. customthe obtained reaction mixture
  2. stirringwas stirred at the same temperature for 1.5 hours
  3. filtrationfollowed by filtration with Celite
  4. customThe solvents were evaporated under reduced pressure from the filtrate
  5. customthe obtained residue was purified with NH-silica gel column chromatography (heptane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-8669f49461d544659887bc2149da102f
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273885B2

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