1,3-Dibromopropane → HCID 92135508, 화합물

HRID 925120

반응식

HRID 925120 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:23][CH2:24][CH2:25]Br>ClCCl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16]#[N:17])[CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 2979634-Benzyloxy-3-methoxyphenylacetonitrile

생성물 1

HCID 92135508HCID 92135508, 화합물수율 50.1%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (3.1 g, 12.24 mmol) in dichloromethane (30 mL) was added sodium hydroxide (30 mL, 50% aqueous solution, 367 mmol), TBAB (0.99 g, 3.06 mmol) and then with 1,3-dibromopropane (2 mL, 19.58 mmol). The reaction was stirred at room temperature for 72 hours. The layers were separated, organic layer was dried (MgSO4) and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (1.8 g, 50%). MS (ESI) m/z 294 (M+H)+.

후처리

  1. customThe layers were separated
  2. dry with materialorganic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography (silica gel, 5-25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-4ba382dbcae64e058b3315ac9ebb5dd1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284272B2

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